Host 0:03
Welcome to The Blogger Genius Podcast, brought to you by MiloTree. Here’s your host, Jillian Leslie.
Jillian Leslie 0:12
Hey guys, welcome back to the show. Today, my guest is a really cool guy. His name is Jason Zook, and he has started some of the most unique businesses I have seen.
He and his wife Caroline have a membership site for people who work with clients. But he just has some interesting thoughts about entrepreneurship, brand building, and when is enough enough in your business.
He got me thinking for days about this interview afterwards and really questioning my own business. I think you’re going to find him incredibly inspiring. So without further ado, here is Jason Zook.
Jason, welcome to the show.
Jason Zook 1:03
Thank you so much for having me.
Jillian Leslie 1:04
Okay, so I reached out to you because our community manager, Paula Rollo, said, “You have to get Jason on the show.” And I reached out to you, I told you that, and you said yeah, you would do it, and so I’m so pleased. So thank you for coming on and sharing what you know.
Jason Zook 1:23
Well, if someone says I have to be, you know, like you have to get this person, how do you turn that down? You know, like I’m not Oprah status yet, obviously. I’m like a million miles away from Oprah status. So when someone says I have to do something, I’m like, “Yeah, well, they said it, I gotta be here.”
Jillian Leslie 1:38
Yeah. And so I started researching you and looking at what you and your wife Caroline have built. And it looks like you are a serial entrepreneur. And you guys have a membership site to help other entrepreneurs find products that they can sell and be inspired.
So, you tell me about that, and then also about your journey.
Jason Zook 2:03
Totally. Yeah, I started my entrepreneurial journey in 2007 and I had never done anything entrepreneurial as a kid. I didn’t have a lemonade stand. I tried to mow one lawn one weekend and it was awful and I stopped doing it.
So this is not something that I grew up around or that I had been doing forever. I had a 9 to 5 job as a graphic designer for 3 1/2 years after going to college, and I was on that path, you know, the corporate ladder path and just doing that thing.
And somehow the book the ‘Purple Cow’ by Seth Godin landed on my desk.
And I just looked around one day and realized, holy crap, everything’s beige, like literally and metaphorically. It was a very blah existence. I didn’t enjoy my work. Everything was actually beige as well, which was just a bummer.
Jillian Leslie 2:48
Love him, yes.
Jason Zook 2:51
And I think I was like four pages in, and I close the book, and put it down, and went, “What am I doing here?” Like, I am a purple cow. I’m a weird person; I’ve always been weird, have always been unique. And I should not be working in a 9 to 5 job that does not provide me any value.
And so from there, I built a 6-month plan to start my own design company with a friend of mine. And we did that. And we grew that company over the course of two years.
And then I got hit with this idea of my closet one day in 2008, where I was looking at all these t-shirts that had these logos on them. I was like, why am I wearing these shirts with other people’s logos? I paid for these shirts and then I’m walking around promoting — and this is ridiculous.
And at the same time, social media was really coming up, you know, Facebook was open platform at that time. Twitter was this little fledgling thing, people didn’t know what you were supposed to do on it yet.
And YouTube, you know, there were no YouTubers. There was no Casey Neistat, you know, putting daily vlogs up and amassing a huge audience and all the other people that have done it.
But I just saw this opportunity to do something on my own, share some stories about small businesses. And so I created this I Wear Your Shirt project. And it was just supposed to be a one-year thing.
I had this really crazy pricing structure where it was $1 on the first day, $2 on the second day, $3 on the third day. And I was going to wear a shirt every single day of the year and then promote those companies on social media, so, tweets and Facebook posts and create videos and all this other stuff.
And you know, it was not an easy road to get that idea out into the world, as you can imagine. Telling people you want to wear t-shirts for a living, a lot of people just kind of roll their eyes and are like, Just go back to doing your design work. You’re good at that.”
But I just knew that I wanted to do something unique and different. And go back to that purple cow thing, and I did it. And I sent a lot of emails. I sent a lot of tweets, I interacted with a lot of people.
And that pricing structure really helped because it showed people they didn’t have to pay much early on and it added up over the year. And I just kept telling people, hey, I think this thing, if I show up every day and create stuff, and I’m interesting, people are going to be interested in a couple months, and then that’ll be worth a couple hundred bucks a day by the end of the year.
And sure enough, that took off. That project did really well for me for five years. At the end, it wasn’t so great. I ended up $100,000 in debt, but I learned so many lessons along the way. I continue to learn so many lessons from that project. And it generated over $1.2 million at this time, which was again, an idea I had in my closet staring at some t-shirts.
Jillian Leslie 5:14
Wow.
Jason Zook 5:16
Yeah, that’s the big kind of beginning part. There’s a lot more to it, but that’s most of it.
Jillian Leslie 5:20
Okay, well, we have to dig in here. Because first of all, what I love is that you found an idea that I bet you, 99% of people would say that is crazy. And yet, you made it happen.
Jason Zook 5:33
Yeah. And I, you know, I had been one of those people who had had the like, “Oh, why didn’t I think of that idea?” You know, you hear those things like, “Oh, why didn’t I think of that?”
And I made one of those, I came up with one of those things. And it continues. People talk about it. I stopped doing it in 2013. And we’re six years after that now, and people still put it on lists of like, can’t believe people get paid for this or, you know, crazy ideas you’ll never believe.
And it’s a little bit of like a pat on the back each time one of those comes up that, like, yeah, I actually came up with one of those silly, crazy things.
Jillian Leslie 6:05
I think that’s amazing. Now, how did you get $100,000 in debt?
Jason Zook 6:09
Well, not knowing how to run a business was the first thing. Cash flow issues were definitely the thing.
So that pricing structure was really cool when it was just me and I had another income so that I could supplement the early months which made almost no money whatsoever.
I mean, the first month, when you add up every single day, it was like $400. None of us are going to be able to live on $400.
And so I, in the second year, brought on a second person. And so, you know, that year, you know, we did over like $150,000 or something like that in revenue, which was amazing.
And I started to do some kind of like bigger deals with bigger companies. And then the third year, you know, I got big for my britches, and was like, okay, I got to go to five people.
And this is the entrepreneur’s dilemma of growing for growth’s sake, or trying to reach different milestones or things because it’s what you see around you and it’s what you think means success is.
And for me, I looked at it like, okay, if I’m making, you know, $150,000 or $200,000 a year from this project, well, I should be making $500,000 a year with more employees, because isn’t that what I’m supposed to do? That’s the Silicon Valley mindset, at least in a very small way.
And so yeah, I brought on four other people, I continued to do it myself. And, you know, then it was just a cash flow thing because it was still a lower pricing structure in the beginning and it worked its way up throughout the year.
And I should have noticed that something was wrong in the first, you know, couple of months, and it was like, I had $30,000 in payroll every month. But I was not making $30,000 until like, the fourth or fifth month of the year.
And so that in itself over the course of basically two and a half years, it just drained my entire cash flow, my entire savings, and it put me in debt with having to wait for certain clients to pay for things.
And I just didn’t know how to manage the day-to-day of expenses and revenues. And it sounds so silly but I have run into this so many times with entrepreneurs that we help and that we talk to, and that we, you know, coach and work through, and other things that we’ve been a part of.
You don’t get taught this. Like, if you take a business class in school or if you even take a business class, you know, online or whatever, so much of it is not relatable to an entrepreneurial business, something where revenues are not consistent or something where expenses are really influx.
And a lot of us just are not taught to download your entire credit card statement, pull up every single expense and look at it every month and go, “Do I need this? Is this something I should be spending money on? Do I have the money to pay for this?”
And so there was just a lot of those really simple lessons. But I think a lot of people listening to this are probably nodding their head going, “Yep, I ran into that.” Or, “Uh-oh, I might be running into this.” That I just didn’t see, I didn’t have the time really. I was running everything.
I was going a million miles an hour not getting any sleep and just doing all this work. And yeah, eventually, I had 10 credit cards that had different amounts on them. My family let me borrow some money. And it was crazy.
That was when I had to draw the line in the sand. When I hit $100,000 in total debt. I was like, okay, it’s time to close this business down. It is not working in the way that it’s going.
And also, I’ve worked almost every single day for five years, literally, almost every single day for five years. I need a break, I have to step away from this.
Jillian Leslie 9:33
Yup. There’s so much there. I personally went to business school. And I will tell you that while I loved it, and I learned a lot and stuff, a lot of the skills that I learned are not directly applicable to being an entrepreneur.
Jason Zook 9:49
Mm-hmm.
Jillian Leslie 9:51
And even taking accounting and all of that. What I will say is, it did make me hyper aware of not being underwater, which is what you were, where you’re spending more than you’re making.
And so we do really look at our expenses and say, okay, is this bringing the return that we need? However, I would say we have also struggled with this idea of when to bring on people because we’re constrained. I always say that the biggest constraints that entrepreneurs have is money and time.
And trying to find the balance there can be difficult.
Jason Zook 10:32
Yeah, and one of the things that I’ve learned and that we talk about a lot, my wife and I, and especially with our new Wandering Aimfully project, which has been the evolution of all these different things that I’ve done over the years and that she’s done.
And we’ve just had all these different, you know, ideas and courses and workshops and books and things that we’ve done, is that it really boils down to knowing who you are. Like, are you an entrepreneur? Are you cut out for this?
Because where you get a 9 to 5 job, and you kind of stay on a path and the path is pretty straight, you know, without some kind of, you know, things that you don’t control the business you work for, controls, it’s pretty straight.
You show up every day, you get paid every week, two weeks, month, whatever it is, that’s the path. You know, you do your work.
An entrepreneur’s path is like, we could be doing something for three months and it can work really well. And then all of a sudden, an algorithm changes or a product is no longer relevant or something is completely different, and now you have to completely pivot or shift or change.
And so I think getting to your point, you know, it’s really something that we talk about a lot of. You’re going to have unknown expenses. You’re going to have unknown trajectories and ways that your path changes. And so you do need to do one of two things.
One, give yourself a cap on how long you can do this. So, hey, I can play in the entrepreneurial sand for six months and maybe I have savings that can do that. Or, and this is not the way that we advocate, but hey, sometimes you have to do it.
I can take on a couple months of debt if I really believe in this thing that I’m doing or trying to do. And again, that’s not the way that we preach it but sometimes it’s just the way that it has to be done.
But you have to have a number that you get to that you go, “That’s it, I tried it.” You know, like I got to my number and I cannot go past that because I’m going to put myself in a place where it’s going to hurt myself and my family and my finances for too many years to come.
Jillian Leslie 12:19
Yeah. And we’ve learned this the hard way, which is to pull up when it’s not working and to say that path didn’t work.
And there’s the idea of sunk cost which is something that you do learn in business school, which is even though, you know, let’s say I’ve lost $3,000 or something didn’t work, I’m not going to stay in it because I’ve already spent $3,000. That’s sunk cost.
So you want to then say, well, that’s gone and I need to switch direction. And that, I mean, it taps into so many things like ego or telling, you know, you tell your friends, “Hey, I’ve got this great idea. I’m going to start my own business. And then six months later to go, “Oh, that didn’t work. Am I a failure?”
Jason Zook 13:06
Yeah. And I wrestled a lot with when I shut down that I Wear Your Shirt project of, you know, am I a failure, is this project a failure.
And I couldn’t get past that until I read Ryan Holiday’s book, The Obstacle is the Way. And that book really framed it differently for me. And I realized that, you know what, that business failing is what needed to happen for me to learn business lessons, entrepreneurial lessons, balance lessons on how to not work every single day because it’s just not physically possible.
And also how to realize, you know what, getting into that $100,000 in debt was actually a good thing. Because had I not learned those lessons with that business, maybe I would have had a different business with different amounts of money, and I would have been a million dollars in debt.
And so that hundred thousand dollars became a big boulder that I had to figure out how to get around. But it also showed my wife and I, hey, we need to do a better job of budgeting. We need to actually have more conversations about our money, how our money is being spent. We need to track it closer.
And we really just adopted a lot of really good practices. And so I think that phrase for me, even if you don’t pick up the book. If you’re listening to this and you’re like, “I don’t want to read another book. I’ve got so many on my Goodreads list or whatever.”
Just thinking of that thing of the obstacle is the way. When something hits you, when something is not the thing that you expected or something goes wrong, re-frame your thinking to “this is an opportunity for me to get better than where I was before, or for me to learn something from this experience.”
And that little bit of stoicism, for me, has just been so helpful in overcoming the ego stuff, the failure stuff, any of these things that they really beat me down or that made me feel like I was a bad person.
As opposed to going “Nope, this is just something we all deal with in different ways. How do I get through it?”
Jillian Leslie 14:49
Oh, absolutely. I always say to people that being an entrepreneur is the most unglamorous thing you can do. It looks glamorous, you know, you being an influencer and then you read about all these influencers and how they’re so burnt out because they have to create content.
But, you know, yeah, I get to go to work in my sweatpants, which is awesome. And I get the freedom and the flexibility to, after this, we’re recording this, I’m going to go meet my husband, David, who’s also my partner for lunch. And that’s awesome.
However, at the end of the day, you know, all of the responsibility is on your shoulders. And that also, you know, somebody said this to me, I thought this was kind of interesting, you know, wow, we have these two companies, and that’s so cool.
And then she’s like, wow, but at the end of the day, you’re sweeping the proverbial storeroom. And I’m like, I am. I’m answering all those emails. I’m doing the accounting, I’m doing crap for this.
Now, for me, it’s worth it. But I always say, if there’s anything else you could do, go do that. And if there isn’t, then be an entrepreneur.
Jason Zook 15:59
Yeah. And, you know, it’s funny, you talked about, like, when do you know to hire people, or when do you know, to grow beyond maybe your little team of one if it’s just you, or you and your partner, or whatever it is.
And I like to think about it is as trying to outsource your weaknesses.
Jillian Leslie 16:14
Ooh, i like that.
Jason Zook 16:14
So my weaknesses are paperwork. I loathe it. I would rather sweep the floors and take the garbage out and clean all the dirty dishes before looking at a single piece of paper.
When I get mail from, like, the IRS or anything, and it’s like you need to fill out Form 947, I want to just burn a house down. Like, that’s how angry it makes me. And I don’t know why. I don’t know where this stems from.
I should probably lay on someone’s couch and talk this through because it’s an unhealthy response that I have to paperwork.
But I’ve realized, okay, I need a bookkeeper who not only keeps the books, because that’s just helpful because I have multiple businesses, so I can’t keep up all of it. And I just need someone who’s better at that, and that they like doing it, I don’t enjoy doing it. But I also need someone who doesn’t mind looking through paperwork.
And so I just started writing out my weaknesses, you know, over the years, and the things that really bummed me out about running my own business. And I think for a lot of people, what you realize is, it’s not that many things.
You know, they’re just a couple of “sweeping the floor” things that you just absolutely hate doing and they really bog you down.
And guess what, the amount of money that you would actually pay someone as a part-time or a virtual assistant, or whatever it is to take those things on is worth its weight in gold.
So for us, my wife had an assistant for a while that was not full time but she basically got paid a similar amount every single month.
I have not had any employees or people that, you know, I would call part time since my I Wear Your Shirt project because it was too much stress and pressure for me to think they relied on me and to have that income loom over my head.
So instead, I love having just a little kind of carousel of freelancers and people who own their own businesses that I can pay a monthly fee or an annual fee, or whatever it is, and they can take these weaknesses of mine and they can do them.
Now, it’s easy to say that when you get into business and you’re making money, and you had expenses, and you can, you know, kind of set these things up.
But I actually tell people from the beginning, hey, find the three things that bother you the most about this. Can you outsource them for a couple hundred dollars a month? Because you should be able to make that a couple hundred dollars a month to pay for that.
But also that will free up your time, your mental energy. And those are the things like you said, time and money, you can’t get any more of just by putting in more effort constantly. There’s different knobs and things you have to turn.
And so yeah, I think that’s one of my biggest recommendations that has helped me over time. It’s just remove those things from the daily entrepreneurial life that give you more time to wear sweatpants, to have lunch with your significant other, to enjoy the moments that an entrepreneurial career provides.
And not force yourself to slog through the things that you absolutely hate doing.
Jillian Leslie 18:56
Absolutely. The way that I think about it and what I tell my audience is to think about, to try to figure out how much you make an hour. And if you can outsource something for less than what you make an hour…
Let’s say you’re a blogger. Let’s say you work with brands and you do sponsored content, you can start… or let’s say, you know, you sell a course or whatever. You can kind of figure out what that number is.
And if you can outsource something for less than that, do it in a heartbeat. Do it in a heartbeat.
Now, there are the things that you’re talking about where it might be more expensive. But if you hate accounting more than anything and it holds you back, absolutely outsource it. And what I do is I go to Upwork, and I hire people for a specific project.
And what I say is, let’s work together for two weeks and we’ll see how we both feel at the end of those two weeks. And if it’s not working, it’s not a good fit. Great, we’ll just part amicably.
But if it is working, you know what, let’s try another project together. And I have found so many great people to help me just by doing that. And if it’s not working, again, to pull up, pull up fast. Don’t try to make it work like a bad marriage.
And that for us has been incredibly helpful. Because hiring people is stressful. Having employees is stressful. You don’t think it is.
Jason Zook 20:28
But it is. And it seems glamorous. Like you said, like there is this era of entrepreneurship that has been kind of cast upon all of us through the magazines and the headlines.
And Gary Vaynerchuk.
And the stories. Yes, all this stuff where it’s like having all these employees and all these things, it makes you look good.
And it’s what I was searching for in, you know, 2011 basically. And I just realized, like, this is not for me, this is not what I want.
And so, you know, it’s interesting, it kind of brings me into a point that I love making nowadays. Because I think it’s so different than the way that most entrepreneurs think. And maybe you’ll align with it because you sound like you’re in alignment with a lot of stuff that we do, is that my wife and I think about things on the terms of “enough”.
So how much money is actually enough for us to make? And let’s really define that based on what we need, not on what we want or what we think is the glamorous number.
So many entrepreneurs are like, I want to make a million dollars, whether that’s a million dollars a year, whether it’s $9 a month, whatever it is, it’s like there’s this number out there that you have that you think about constantly.
And if you really break down why — why do I want that number? Because what is it going to take for me to get it, and am I willing to put that in for what sacrifices am I going to have to make in my life?
Instead of going, and this is what we do, is we go what’s our “MMM” number and that’s your monthly minimum magic number. So that’s just your bare-bones expenses, your living expenses, and then whatever it takes to operate your business.
You’re not doing any savings, you’re not doing anything else. That’s just your bare-bones minimum number.
Okay, that’s a number you definitely want to reach so that you can sustain moving forward. It’d be better to have savings and other things. But like that’s just our minimum number.
Then let’s pick our “enough” number. And let’s add in some things that would make us feel like we have abundance in our life, that make us feel like the work is all worth it.
And that number, what you find is it doesn’t go from let’s say, your MMM number was $5,000 a month. It doesn’t go from $5000 to $50,000 a month or 5 to 100, you know, it really doesn’t.
And when you think about it that way, when you actually look at it, you start to realize, you know what, I am buying into all the platitudes. I am buying into all the hype and the things that people are telling me that I think I should want.
I don’t need that. What I would love to be comfortable with is $20,000 a month, that would be amazing. That’s four times the amount of money that I’m currently trying to make.
And if that is my big goal number, that number is so much less hairy and scary than the arbitrary number that keeps us distracted from something that is an achievable goal.
And this idea of enough is something that you see so much in like the minimalism movement now. You see so much in like Marie Kondo who has just taken over everyone’s lives now.
But you see this thing and it’s a movement that we are proud to have jumped on really early, we’re proud to be a part of, and we have a public kind of journey to enough, you know, what our number is –on our website that you can read about.
And the goal for us is just to get to that point and go, okay, we don’t have to try and make any more money. We are done with the trying to make money thing,
it’s not going to happen overnight. We’re nine months into the journey of trying to reach our number. And I think we probably have another year until we’re going to get there. But we have a number that is realistic for us.
Jillian Leslie 23:42
I like that. I like digging deep into why a million dollars. Like, is it so that your parents will finally say, you’re good enough? Is it so that your neighbors think somehow you’re fancy?
And really dissecting that. I mean, I try to be very transparent about how not glamorous It is to be an entrepreneur but how satisfying it is.
And the thing that I struggle with is stopping and saying, “Wow, look at what we’ve accomplished.” Because it’s so easy to be focused on that big number or that big number of followers that you’re trying to get. “If only I can get there, then I’ll be happy.”
If only I, you know, if only… I don’t know, somebody says this thing that I’m dying for them to say that I’m good enough, I’ll be happy.
And it’s about taking that moment to say, Oh, my God, look how far I’ve come. You know, if my MMM number is 5000 and I hit it, holy crap, that’s amazing.
So for me, it’s about stepping back and, you know, thinking about the things that I’m grateful for. Because it’s so easy as an entrepreneur to get lost in the crap of it, in the in the hustle, in the “Oh my God, I’ve got more emails to respond to.” That kind of thing.
And I believe that that is the difference between happiness and sadness as an entrepreneur.
Jason Zook 25:17
Yeah, there’s a really interesting… there’s two thoughts that have been kind of rolling around in my head these past couple months.
One is, we’re also trying to transition from the idea of running a business to walking a business. And it’s this idea of like, why do we have to feel like we’re constantly on this hamster wheel that cannot slow down?
And why do we have to feel like we’re, you know, always running to meetings or calls or our schedules are overbooked, or all these things. And it just feels like you’re running constantly.
And why can’t you go to a walking pace; why can’t you slow down.
And this is one thing that it’s easier said than done. A hundred percent, you know, will admit to that. And you may have to run in the beginning to get to a place where you can walk. That is just the truth of it.
But if your mindset again, is like with the enough number, where you go, here is what I want my day to look like, here is how many hours I want to be working that is realistic to have the results of my business that I think I can have, then you work toward that.
And yeah, you may need to “hustle” a little bit in the beginning. You may need to have a little bit of a hustle period.
But then, you know what, you flip the hustle off. You turn it off, and you go, I am okay with working two hours today. And I’m not going to feel guilty. I’m not going to feel like I didn’t deserve to do this. And I could have been doing more.
I’m going to say that this is okay. And so that little reframing for us is also something that we’re working toward. And I have an article that is like, three quarters of the way done, but I don’t know how to finish it. So I’m trying to figure out finish it.
But it’s also because we’re not 100% doing that yet. So I feel like a little bit of that impostor syndrome of “Okay, I like this idea, but haven’t quite figured out yet.” So I’m going to finish that soon.
The other idea is, is the way that I like to think about a time profitability.
So it’s very easy to understand profitability in business. It’s just you have revenue minus your expenses, that’s your profit. There’s a lot more nuance to that, obviously.
But with time, it’s kind of interesting in that we don’t think about time as something with profit as well. And we can look at running our own businesses and going “Well, I worked nine hours today.”
And it’s like, yeah, you did, but none of it was fun. None of it did you actually enjoy. None of it felt like profit. None of it felt like the abundance that has come from the amount of work that you’ve put in.
And I think one of the things that you touched on that we think about all the time is, you know, if you want to make a million dollars, what does it actually take? And are you going to be time poor and you’re never going to have time profit?
Because all you’re doing is pushing yourself to get to this arbitrary amount of money, not realizing, number one, that your expenses are going to go up tenfold to get to that money. That’s one thing people just never think about.
They just think I’m going to run my business right now. Same amount of expenses but I’m eventually going to have a million dollars in revenue and then that’s going to be, you know, a lot of profit.
It doesn’t work that way. All the things ratchet up equally for most of us to get to that point. I know because I watched it happen for myself.
But if you can get to a place where you realize, you know what, having some free time and having that time profit kind of built into my life is actually going to make me feel like maybe even the small amount of profit that I do have in my business, if my business only makes $100,000 a year.
But it doesn’t cost me $90,000 to do that. It cost me a lot less than that. And I have all this extra time or at least have good breathing room. That is something that it’s kind of like touching the hot burner on the stove as a kid.
You can tell a kid 100 times “don’t touch that, it’s hot. Don’t touch that, it’s hot.”
But guess what they have to do to understand how painful it is, the thing that you’ve told them. They have to touch the hot stove.
And I feel like for every entrepreneur, you know, we said these messages in many different forms. We have a community now that we interact with. We tell them all these things constantly.
But I think for everybody, it’s your own touching of the hot stove that you have to experience in some way to go “Oh, okay, here it is. My time is not profitable.”
I am just running my business constantly. And I am chasing a whole lot of societal pressures and norms, as opposed to looking within on what really matters to me.
Jillian Leslie 29:20
Oh, I couldn’t agree more. And the thing that you were saying that something I have been thinking about a lot, is how you’re running your business, and you’re running, and you’re running, and you’re running.
And in the process of that, you constantly feel like you’re falling short. It doesn’t matter how much you are running. You are sprinting. But there is this mindset of “And I’m falling short.”
And I think about that. And in fact, we have a daughter, and she’s 11. And I’m watching her grow up. And people say this when you have a child that in the beginning, it’s like watching paint dry.
It is the slowest thing, getting through that first year, at least for us, was really hard and really slow. And you think to yourself, “Oh, my God, what have we gotten ourselves into? This is going to be a lifetime.”
And then all of a sudden, they hit like 11. And you can see that they’re now getting to be fully formed people and that they’re kind of on their way out. And it is so bittersweet is the way that I would describe it. And it’s making me want to cherish moments more.
And so I’m working on the mindset of running, running, running, falling short and saying to myself, maybe I’m not falling short and maybe I don’t need to run so hard. And maybe I want to suck up this moment.
Because I’m seeing the moments, the infinite number of moments shrinking and they’re not infinite anymore. And I’m really trying to think about that shift for myself.
Jason Zook 30:57
My wife likes to say, what is it all for? You know, like, what are all the working hours? What are all the long nights? What are all the weekends spent away from spending time with your kids or your family or your hobbies or whatever. Like, what’s it for?
Do you think you’re just going to put in three years of really hard work and then you’re going to enjoy it for the next 30? Show me the pictures of the people who’ve done that. Tell me the stories of the people who actually enjoy their lives after they’ve gotten to those points. It’s very far and few between.
And those are the outliers. Those are not the norm, which is the majority of us.
Jillian Leslie 31:32
Just the idea that the more you have, the more you have to worry about. Like, your problems don’t go away because you have a million dollars in the bank. And in fact, you can create more.
Jason Zook 31:44
I’m living proof of it. I’ve been there. I know what it felt like to have, you know, $30,000 in expenses go out every single month or $30,000 in salaries go out and not including expenses.
So like those pressures, when you ratchet up your business and when you’re trying to hit these milestones.
And that’s why we really are trying to focus on this whole idea of enough. And this idea of enough is different for everybody. It’s everyone’s own journey. But it’s the right way to think about this if you are an entrepreneur.
It is not buying into the venture capital mindset. It is not buying into the scale your company for scale’s sake, and hit numbers for number’s sake,
It’s about, what do you want in your life? What are the things that really matter to you?
And if you can clearly identify those, being with your kids going to lunch whenever you want, wearing copious amounts of sweatpants, you know, just travel. All the things that you actually write down that matter to you.
And if you can start to look back at that list and go, you know what, I’m actually doing all these things. Like, yeah, it’s stressful to run my business at times. That’s just going to be the nature of owning your own business. It’s never going to be set it and forget it forever.
And so you just have to take that moment to understand, “I am doing what I want to be doing, you know, there’s really nothing else that matters to me when I really think about it that I want to be doing. And I’ve made it.” And that’s a funny phrase that so many of us are afraid to say as entrepreneurs.
Jillian Leslie 33:10
I like that. Yes, I’ve made it.
Jason Zook 33:12
Yeah. And I said it at a… I went to a mastermind group with a bunch of guys here in Southern California a couple years ago. And I don’t really love the idea of mastermind groups because I feel like a lot of people who make masterminds are neither masters of anything.
Nor are they really mindful about anything. So it’s very, like, it just bothers me.
Anyway, I went to this group, a bunch of really successful guys. And I sat around listening to all the things all of them wanted. We sat around this table with everyone going around saying like, what do you want for your business, like, blah, blah, blah. And everybody wanted more.
And this was before we had started kind of really identifying the enough thing.
And I just sat there, I thought to myself, and I looked around at them. And I was like, I’m four years removed from my I Wear Your Shirt “failure”.
I have developed a business that makes about a quarter of a million dollars a year that is very profitable.
I have very little expenses, and I live where I want to live. My wife and I are very happy. We do what we want to do. We have very flexible schedules. We have an amazing community of people.
And I just sat there and it came on to me, and I was like, Guys, you probably all are going to want me to leave after I say this, but I think I’ve made it.
And they were stunned. None of them knew what to say. Because all of them are saying, Oh, I want to get from 9 employees to 12 employees in the next three years. And I want to get my $500,000 client to a $1.5 million client.
And it’s just all these things. And I was like, that’s not for me. That’s not what I want. It’s not what’s going to make me happy and I don’t think it’s going to be what make you guys happy either but you’re just not willing to admit it.
And so this idea of you can really clearly identify the things that you want in your life and if you’re hitting those things in any capacity, and you can tell yourself and say out loud and look yourself in the mirror, and it might feel weird, but to go, “I’ve made it. I am where I wanted to get to.”
Jillian Leslie 34:52
I have to tell you when you first just said that, it gave me chills.
It really did. I think there’s something really powerful. I think that as an entrepreneur, not only do you need to manage the books but you need to manage your own brain.
You need to manage the stories you tell yourself. I say this to my daughter all the time because she’ll come home and say, “Tomorrow is going to be the worst day.” And I go, “Really?” I go, “That’s a really interesting story. How do you know that? What if it’s the best day?”
And I see it of course, it’s easy to see it in my daughter. It’s much harder to do it for yourself.
But again, just saying that of it’s enough and I’ve made it. I mean, wow, how powerful. Because we’re taught never to say that. What we’re taught is to say, I’m falling short and there’s not enough time and there’s not enough money and we’re living in scarcity.
Jason Zook 35:48
Yep. Yeah. I was going to say, so we have this membership community that you talked about very early on. And it’s only been around now for… it’s been around for about three years, but in very different iterations. But now it’s like an official thing for the past nine months. And we go through this exercise with almost every single person in the community, whether it’s direct, or whether they find it themselves, or whatever. And so many of them are blown away when they realize that they’ve made it as well that they are living the life that they want. And that doesn’t mean that they have financial security forever. That’s just for an entrepreneur I’m sorry, it’s probably never going to be a thing for most i agree i agree it’s gonna be it’s gonna be something you just have to fight for at it on a constant basis. But if you have the rest of your stuff in life, and in your business set up in a way that you are really happy every day, or you can see that happiness is achievable in the next couple months based on your plans, then you’ve made it you’re there there is no other finish line that you’re going to get to that’s going to make you feel any better than where you are right now. And so if you feel good about where you are right now, it makes it so much easier to get through the obstacles that come up to get through the tough times that hit you know, to have the things in your business go wrong that inevitably go wrong for all of us and you can at least come back to that and go Okay, like I’m veered a little bit off course you know, maybe I’m not feeling like I’ve made it right now I’m a little bit behind but that’s okay it’s only going to take these couple of things to get me back to where I was and that’s achievable that’s not a pie in the sky thing that’s a I have a month that I need to you know invest doing x y&z to make it happen.
It’s going to be something you just have to fight for on a constant basis. But if you have the rest of your stuff in life and in your business set up in a way that you are really happy every day, or you can see that happiness is achievable in the next couple months based on your plans, then you’ve made it.
You’re there. There is no other finish line that you’re going to get to that’s going to make you feel any better than where you are right now. And so if you feel good about where you are right now, it makes it so much easier to get through the obstacles that come up to get through the tough times that hit.
And we go through this exercise with almost every single person in the community, whether it’s direct, or whether they find it themselves, or whatever. And so many of them are blown away when they realize that they’ve made it as well, that they are living the life that they want.
And that doesn’t mean that they have financial security forever. That’s just for an entrepreneur, I’m sorry, it’s probably never going to be a thing for mostof us.
Jillian Leslie 36:59
I agree, i agree.
Jason Zook 36:59
You know, to have the things in your business go wrong that inevitably go wrong for all of us and you can at least come back to that and go, Okay, like I’ve veered a little bit off course. You know, maybe I’m not feeling like I’ve made it right now, I’m a little bit behind.
But that’s okay. It’s only going to take these couple of things to get me back to where I was. And that’s achievable. That’s not a pie-in-the-sky thing. That’s a “I have a month that I need to invest doing X, Y, and Z to make it happen.”
Jillian Leslie 37:24
I wanted to take a short break to talk about MiloTree. If you’re trying to grow your followers, your subscribers because you want to grow your traffic, because you want to grow your engagement, MiloTree is your tool.
I welcome you to head to MiloTree.com, sign up for a free account. You get your first 30 days free. And you can grow Instagram, Pinterest, Facebook, YouTube, your Shopify sales, and your email list all from this service.
After your first 30 days free, it is $9 a month and you get all these different pop ups. And you get added to my personal newsletter where I send out tips and tricks and what I’m thinking about. So, go try it. And now back to the show.
So talk to me about burnout. Because I know you’ve talked about it and, you know, just perusing your stuff. That’s something that you really try to address.
Jason Zook 38:25
Yeah. Man, my wife and I both experienced it in different ways. I really experienced it with my I Wear Your Shirt project because I filmed a YouTube video every single day, pretty much almost every day for 1600 days straight.
Jillian Leslie 38:39
Oh my god, yeah.
Jason Zook 38:40
And again, this is before ,like, YouTubers were a thing. This is before daily vlogging was a thing in our kind of culture that people understood.
And for four years, I couldn’t look at a camera.
I bet, I bet.
I made a couple of videos here and there and it always just hurt my soul. It hurt my soul to record, to edit, to publish. I just hated it.
And I finally got to this point where I think just enough time had passed. And I think if anybody’s gone through any burnout, you kind of know, it’s just time that heals burnout. I mean, there’s nothing else.
You need space away from whatever thing burns you out to be able to get back to it. But for me, when I finally kind of came back around, it was really setting some hard parameters about what I was going to do if I was going to start doing video again.
And so that became a much more relaxed schedule, that became a much lower pressure for me to deliver a super high quality product that I was comparing myself to other people. You know, those comparison traps that we all fall into over and over again.
And so this whole idea of burnout for me is just something that I’ve seen happen over and over again. And it’s why we created this, we have a six-month program now that’s actually starting in March called Build Without Burnout Academy.
And the idea is that we want to help people who they want to make a digital product of some sort, whether it’s an online course, or an e-book, or a membership community, or just any product that they want to make.
And they want a plan of action that is not going to burn them out. Because it takes a lot of things to get to launching things successfully and making money from it. It takes building an audience, it takes getting your expenses in revenues all in order.
It takes understanding your product market fit. It takes creating content. And each one of those things, you can experience burnout with.
And so my wife and I really sat down and looked at how can we do this in a way where we’ve learned from our experiences, we can apply that and we can stretch this out, not because we want people to take a longer amount of time, because everybody wants things done as fast as possible. We do too.
But so that you understand, I’m going to commit to doing something. I’m going to get to this goal that I want to reach, but I am not going to hate it along the way.
I am not going to get to the end and then go “I can’t do this for another couple years.”
Because you’ve now built something that’s not sustainable. And for us entrepreneurs, we need stuff that can sustain, we need stuff that we can go back to and relaunch or re-promote or re-sell. You know, whatever those things are, so that we can continue to generate revenue and to make happy customers.
And so for us, yeah, we built this six months program based on our experience. It’s something that’s been really fun to put together because it’s challenged a lot of our own assumptions about what it takes to do these things, how fast you can get them done.
And also just being realistic about what it takes to build a business for yourself. And what it takes to build a revenue generating thing. And it does take time and it does take effort. But you don’t have to burn the candle at all the ends to make that happen.
Jillian Leslie 41:38
Yes. And I always speak to I started to save them in my inbox, the emails that promise that you’re going to be a millionaire when you launch your course — and how that is so not true.
And you know, people say to us, like, wow, how did you grow your social media so big? Right? We just crossed over for one of our companies a million followers on Pinterest, for example.
And I say to them, I go, it’s a long… I’ve said this before. It’s a long slog. And if there were a magic bullet, you better believe I’d be using it.
So do not buy into this idea that somehow, you know, you’re going to kill yourself, and then boom, you’re going to make a million dollars. And then when it doesn’t happen, don’t be surprised.
Jason Zook 42:29
Yeah. Yep.
Jillian Leslie 42:32
That it is about pacing. And it is about just stepping back and giving yourself credit for how far you’ve come.
Jason Zook 42:41
Yeah. And you can make a million dollars with a course launch if you want. But guess what, you’re going to hate your life in the process. You’re going to not want to touch that course afterwards. You may not enjoy the customers that you have to attract, to make that happen.
I mean, there’s just so many things that again, it’s the hot stove thing. It’s this like, you can say it over and over again. But unless someone kind of figures out and goes through it…
And that’s actually why this Build Without Burnout program, for us, it has been really interesting too, because we’re just about to kick it off. And we just kind of sold our first group of people into it.
I think every single person who bought was like, “I had burned out before, I have fallen into the trappings of thinking I can do everything overnight.”
Like this is a refreshing, different look at thinking about this, as opposed to just falling into another, you know, someone selling me the dream and thinking that tomorrow I can flip on some switch and I’m going to have all this money falling.
Jillian Leslie 43:29
Yes. That there’s a magic bullet, and there isn’t. And therefore I always say, well, it takes a lot of work and it takes being in there day in and day out. But you’re right, the piece that I’m not thinking about or talking about is how to stay in it day in and day out in a healthy way so you don’t hate your life.
Jason Zook 43:51
Yep.
Jillian Leslie 43:52
I think that is so valuable, so powerful. Honestly, I’ve just, you know, I’ve learned so much just talking to you about all this stuff.
Jason Zook 44:02
Awesome. Well, I’ve learned a lot of lessons the hard way and I’m happy to share all of my mistakes. And that’s one thing that we strongly believe in.
And if you go to Wanderingaimfully.com, you will clearly see that we are not afraid to share every detail, every honest and truthful thing, the good, the bad, the ugly. And just I think we need more of that in the entrepreneurial space.
We need less of the “here’s my perfect curated life and I make $100,000 a month doing nothing.” Because it’s not realistic.
And I think that for the majority of us, it’s about figuring out our enough numbers. It’s about figuring out how we can transition into walking our businesses. And it’s about trying to have that time profitability, trying to know that each day. your hours are your own, and you enjoy what you do. It’s the journey we’re on.
Jillian Leslie 44:52
Yes, it’s about celebrating those successes. And it is about when you feel like you’re falling short, go take yourself out for lunch. You know, touching yourself with a sense of compassion, and that you are enough.
Honestly, Jason, thank you so much. So please, share how people can reach out to you and Caroline, and learn more about what you’re doing because I feel like you are putting good into the world.
Jason Zook 45:19
Yeah, if anybody wants to kind of read the stuff that we put out to the world or watch our recent videos, we have our own show and podcast called Wandering Aimfully: The Show.
It’s an incredibly, you know, secretive name. But WanderingAimfully.com is the easiest place to find all of our stuff. You could find me Jason Zook on Twitter or Instagram.
Although I do take frequent breaks from social media, I take detoxes, which is really fun. That’s probably a whole another topic for another show.
But yeah, you know, I would just say, if you want to reach out to us, if you have any questions, I am an open book. My email is very easy to find. Contact form on our site is really easy to use.
So I would love to hear stories from people who’ve listened to this and maybe it’s, you know, had some changes come their way. Or if they’re just like, “Hey, you were talking about this. Do you have an article on it or anything that can help me?” I’m happy to pass along some stuff to your listeners.
And yeah, just thank you for the opportunity and the good convo.
Jillian Leslie 46:09
Oh, wow. Well, Jason, thank you so much for being on the show.
Guys, if you like the show, please subscribe. Please leave comments, messages, whatever. Let people know about it. And I will see you again here next week.
Transcribed by https://otter.ai