305: Non-Traditional Success – Optimizing for Happiness with Jason Glaspey

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An image of trophies and the title of Jason Glaspey's episode on the Food Blogger Pro Podcast, 'Non-Traditional Success.'

Welcome to episode 305 of The Food Blogger Pro Podcast! This week on the podcast, Bjork interviews Jason Glaspey about optimizing your life and business for maximum happiness.

Last week on the podcast, we re-shared our episode with Frosting and Fettuccine’s Sam Adler where she talks about creating the very best content for her audience. To go back and listen to that episode, click here.

Optimizing for Happiness 

How do you define success with your blog or business?

It’s an interesting question to think about, especially as you dive into different business growth strategies.

Jason is here today to talk about how he measures success and how that influences the way he views business and spends his time.

It’s a fascinating conversation, and we’re hoping it’ll help you figure out how you can do more of the work that you enjoy.

A quote from Jason Glaspey’s appearance on the Food Blogger Pro podcast that says, 'My career isn't actually nearly as important as the lifestyle my wife and I choose together... and we want to work towards that outcome as a team.'

In this episode, you’ll learn:

  • What it was like to sell a business
  • How he found balance as an entrepreneur
  • How he decided to sell a business
  • How he comes up with new business ideas
  • How to do the work you enjoy and change what you’re optimizing
  • How to define what you want
  • How Webflow can help you build websites
  • How to connect with others online


If you have any comments, questions, or suggestions for interviews, be sure to email them to [email protected].

Learn more about joining the Food Blogger Pro community!

Transcript (click to expand):

Bjork Ostrom: Ladies and gentlemen, I’m really excited to be talking to somebody who just today I was sorting my contacts, Jason. I’m using this, I’m in the beta stage. I know you’re a beta user of a lot of software. I was beta testing this app called Folk, which is content management, and your name came up. You have to categorize people, and there’s business, and there’s blogging, and I categorize you as friend. So I just want you to know, that’s where you landed.

Bjork Ostrom: But for those who aren’t familiar with Jason, podcast listeners, Jason is a friend but also somebody who’s had success in business, who’s a creative thinker, who’s really connected. And I’m excited to talk to you, Jason, about your story because you’ve been at this for a really long time. When we last connected, I heard of this app, it was like this pub crawling app kind of thing. I’m probably doing a bad job explaining it, but you’ve been in the world of online businesses and online ideas for a long time and have had some really cool successes with that.

Bjork Ostrom: And you’re also a really good connector of people, which I’m interested to hear about your story. And in the food space as well. We’re going to be talking about PaleoPlan. And today actually is, what did you call it, the saleaversary of one of the businesses that you created, built, scaled and sold, PaleoPlan. How long ago was that and what was that day like when you sell your business? And then do you just get a really big check in your bank account? How does that work?

Jason Glaspey: Yeah. It was seven years ago. At the time, my wife and I, we were spending a month in Mexico. We live here now, but at the time we were still just kind of dabbling. My wife’s parents were in town, and it was the day they left. And everything was supposed to go through some time, and they were like, “Yeah. There should be a wire hit your bank account,” because nothing feels real until you have money. And then eventually, the guy to pick up my wife’s parents to take them to the airport had just pulled up, and I checked, and it was like the money was there. And we were like, “Shots of tequila quick.” We did a frantic round of shots and hugs, and crying and high fives. They left, and my wife and I looked at each other, and we had a two-year-old at the time, and we were like, “I guess we’ll go to the beach.” And went to the beach and hung out. It was a pretty awesome day.

Bjork Ostrom: You hear that with athletes who sign a big contract, and it’s like, “What do you do after you sign this huge contract?” And a lot of times they’re like, “Went to McDonald’s and got a Big Mac.” And then it’s just like back to normal, but what did that look like for you, because previously your normal had been working on this site and this business? So what does the next day look like after you sell something?

Jason Glaspey: Yeah. That is a question I didn’t even know I needed to think about. When the time came, I was pretty convinced like, “Hey, I’m going to take a little bit of time off. I don’t need to work tomorrow.” I think I took a month off before I really asked myself next questions. But you’re definitely just vibrating, you’re excited. But there’s also in some ways just like, “Holy crap. What am I going to do now? What do I do?” It doesn’t have to be super specific, but it wasn’t like forever changing money. It was a couple of years changing money. The equivalent of like 5% year salary. So like, “Wow.” Normally you don’t get that all once. And I didn’t get it all at once also a part of it.

Jason Glaspey: So there’s all this excitement, but still a sense of like, “I’m certainly not retired. I certainly don’t have few money.” So there’s this feeling of, “Can I do it again? And how quickly do I need to do it again?” And the sense of my ego got involved, and I wanted to prove I could do it again. So there’s all these weird calls on your emotions, and you have to really start making decisions about who you are, what your values are, how you’re going to define yourself and your time, because you have suddenly a little bit more breathing room to think about some things, and you have a little bit more responsibility because you get the privilege of choosing a little bit more about who you are and your lifestyle when you’re not suddenly forced to be on someone else’s clock.

Jason Glaspey: And I’d already been kind of free from someone else’s clock for about three years at that point. I ran PaleoPlan for five years, and about a year and a half into it, I broke off full-time. I mean, close to two years. But that sense of moving forward, moving forward, moving forward, and then suddenly you send your baby to college, and the house is quiet and you don’t really know what your identity is anymore.

Bjork Ostrom: Yeah, yeah. It’s a good analogy. Did you feel that was true for you in that season, the year or two after where it was like, “Who am I and what am I about?”?

Jason Glaspey: Yeah. I had a really good idea who I thought I was, and I just ran after that person really quickly. It turns out, I think I’m a different person than I thought I was, and I have changed a lot of the perspectives I had from seven years ago, hopefully.

Bjork Ostrom: Who did you think you were and who are you? This is getting deep quick.

Jason Glaspey: There’s no way I can answer that without sounding pretentious. But I think I felt like I needed to be this hyper successful guy. I needed to show everyone like, “You didn’t have to take VC money to run a company and have a small exit that was meaningful.” Seven years ago, the startup world was different, how people thought about companies was still different. The whole world, startup felt different, and I didn’t necessarily qualify, and I felt a lot of ego about that, because I didn’t want to call what I had a side hustle. It was bigger than that. And for some reason, I was just really worried about what other people thought, what the titles were, how I define myself with words to the outside world, instead of actually just caring about who I think I am, and what are the values that I care about, and how am I living those out with my family every day?

Bjork Ostrom: Do you feel you’ve been able to make that transition now where that’s more aligned?

Jason Glaspey: Yeah, actually. I mean, this year was pretty crazy year for I’m sure almost everyone. But my family, my wife and I especially really doubled down and recognized, “Hey, we’re a team. We’re doing this together.” My career isn’t actually nearly as important as the lifestyle my wife and I choose together, and that we want to work towards that outcome as a team versus working towards who’s Jason Glaspey and what defines him as a person? And how do I let the world know about that? I just really quit caring about it, and I just care about like, “Hey, do I have a chance to live amongst community people that I care about? Do I create things that matter, that help other people? And am I doing it in total partnership with my family?” That’s what matters, not necessarily the title of, “I sold something at X multiple.”

Bjork Ostrom: Yeah. I think there’s extreme freedom that comes from not holding so tightly to how you’re perceived in the world, and also knowing that… I was having this conversation with my dad the other day, and was reflecting on this, the dual reality of everything we do is insignificant, and everything we do is eternally significant. The things that we do have an impact, and they can make the world a better place, and they can impact people in really significant ways. And yet, it’s not us, it’s not me, it’s not Bjork Ostrom or Jason Glaspey is the reason that’s significant, it’s because we can do work that can impact people. But also I know that like in a minute, I will be forgotten once I’m gone.

Bjork Ostrom: And I think those two things are so true. And maybe it sounds a little bit more, but I think I’m relating to what you’re saying in that, there’s something centering about it, I think to release some of the weightiness of needing to be known and to prove something, whatever that might be. While not saying nothing matters, I’m just going to shrug and not try and do anything, like holding those things true. Does that resonate with in the vicinity of what you’re getting at?

Jason Glaspey: Totally. Yeah. I definitely transitioned from, and it’s not that I don’t care about what people think of who I am, I just recognize that like, “Hey, I’m just going to be the most me I can be. And I’m going to do it in a way that honors and respects other people, and the world around me, all things included.” And I don’t have to manage my reputation, so to speak. Be the person I want to be, and that’s how I’ll be defined.

Bjork Ostrom: Yeah, yeah. One of the concepts we talk about on the podcast occasionally, is this idea of really clearly understanding where you’re trying to go, and then knowing that you don’t have to take somebody else’s path to get there. And I think sometimes what I see myself doing is, I see somewhere that I want to go and I see somebody who’s maybe gotten there, and then I think that’s the path that I have to take to get there. But what I hear you saying is, “Hey, understand who you are and where you want to go for you.” You talked about that as really having a good idea of what living a good life with your family looks like. And then saying like, “Okay. With me being who I am and how I work within the world, how do I get there?” As opposed to saying like, “I see somebody else who did that, maybe I need to go that way.”

Bjork Ostrom: That’s been something significant for me as I’ve gone through the process. And I think one of the ways that we do that is by hearing stories, but then also knowing what our story is within that. I want to talk specifically about PaleoPlan because I think some people’s story, they want to replicate what you did. They want to build something, they want to either then work on it for a long period of time and maybe create autonomy within their work and cash flow within the business. And you did that. Why did you decide to sell? Why not continue to run a company forever? How do you know when it’s time to not do it anymore?

Jason Glaspey: Yeah. I mean, there’s a lot of parts to that question. Part of what made me want to start PaleoPlan was in 2009, when I started it, I was following the Paleo diet, and information was super hard to get about it at the time. There were a couple of books and one or two websites, and it was very difficult to actually just find the information. Straight up, “Is this recipe paleo? Is quinoa paleo? Why not? What am I going to eat this week? How do I find some recipes?” And so just doing that work was labor. And I recognized that, “Man, anyone who’s trying to eat paleo right now is going through the exact same thing as I am. They have no better resources than I do.” I’m very good at Google, so I trust my ability to find things on the Internet, at least as well as most people.

Jason Glaspey: And I just realized like, “Hey, other people are wasting time doing the exact same thing as I am. If I can share this thing that I’ve had to work to get, that immediately works for other people, then there’s value there.” And I hate that word like capital V value in a capitalistic way, but there’s just like I’m helping people. And for those who don’t know, PaleoPlan was a meal planning service. So we emailed you meal plans, shopping lists and recipes once a week for $10 a month. And it just solved how to eat a paleo problem. Again, in 2009, that problem wasn’t being solved by anyone else in a convenient way, and my tool took off. I was fortunate to get in there early, and I ranked number one for paleo recipes for several years. And as a result, we just got a lot of people who were looking to solve that problem.

Jason Glaspey: That part has been super powerful, and just like I always want to go back to that. I don’t want to just find a way where a transaction is occurring and I can take a little part of it. Like, “Here is a totally mundane product, and I’m going to sell it but I’m going to figure out just one technique better to sell it.” And almost all of the energies is going into convincing people to just buy mine over someone else’s. I’ve done that and I don’t enjoy that. And so I’d much rather be like, “Hey, how can I actually use my creativity, the things that I love doing, writing things, making things into something that helps other people?” Well, at the same time it stems from there was a real need because I had struggled to find the information myself.

Jason Glaspey: But after a certain point, I mean, I’m not the face of paleo nation. I do still like beer, I’m not dogmatic about what I eat. And I definitely had also run the company to the extent that my skills were currently able to push it forward. And you feel guilty having this thing that is valuable, but you don’t know what to do with it. And it weighed on me as an entrepreneur that I wasn’t maximizing it’s potential, but I wasn’t really sure what to do, nor did I want to risk the energy of trying to increase my revenue with a bunch of things that I had no idea if it would work. And it just seemed like paleo was not going to last forever. In this case, there was a fad nature to it, where the majority of the popularity came and left. There’s still millions of people eating it, but I recognized also that there would be a time when it wasn’t as valuable as it was right then.

Bjork Ostrom: If you look at Google Trends and type in paleo, or paleo versus keto, or whatever it might be, you can see that. So smart on your part. It’s still around, do you know who it’s with right now and kind of the story of it? Or do you after you sell something, it’s kind of like, “Hey, I’m done. I’m going to step back.”?

Jason Glaspey: Yeah. I maintained a small share of the company after I sold it, and there was a buyout period where they were paying every month. So I was definitely aware of what was happening. And the person who bought it, I think he realized a lot of his skill sets matched mine. And so what he brought were things that I had kind of already optimized. And I think that he struggled to find, what is the next step for it as well. And then he ended up selling it onto another company. And those people had a handful of other paleo properties. So this was kind of a, “Oh, this is a great tool to use with all of our other things. When we get people in, we now have another product to sell.” So he ended up passing it along after just a year or two. And I believe it’s still going strong. I check it every once in a while. It looks very similar than it did when I sold it.

Bjork Ostrom: Sure. That makes sense. How much of what you’re doing now is trying to catch a similar wave? Because I think there’s something to be said about, if you have the best copy, the best product, the best customer support in an industry that’s non-existent or declining, it’s really difficult. If you have like all of that stuff in an industry that’s on the rise, or even average product, average customer service, average all the things in a really significant industry trend, I think that can almost be more important than all of the other things, as long as eventually those things come along, product, marketing, all of that.

Bjork Ostrom: When you think of new ideas now, how much of it is like, “Hey, can I find this thing that is happening in the world, online or offline? And can I catch that wave in a similar way to maybe what paleo was?” Not necessarily in the food space, but is that part of your thinking, having in some ways kind of experienced that? Or was that not part of PaleoPlan when you look back at it?

Jason Glaspey: No. The majority of my success, I think came from two elements that just blended well. One was, I recognized that paleo was being promoted by the CrossFit gyms. And I knew that CrossFit was exploding and that meant that PaleoPlan was going to get promoted to a lot of really healthy, really fit people who wanted an optimized edge, and those people who a lot of out of shape people go to for advice. So when you look at a really ripped dude from CrossFit, you’re like, “What’s the secret, man?” He’s like, “I eat paleo and I go to this gym.” I was like, “This is going to grow. This is going to grow naturally in the shadow of this other wave that has a lot of money behind it.”

Jason Glaspey: And I recognized that, I recognized that at the time there were really low resources and I was really good at building websites. I mean, I was a professional website builder going into that. So I knew how to do it, I knew how to think about it from a product perspective, and like, what do customers actually want? And how do we actually give that to them in a simple way versus a complicated way? Having empathy for the end user and their experience, and actually really caring about that, is honestly the superpower. All you have to do is really care. And so to answer your question, I have found myself throughout the past couple of years presented with infinite opportunities.

Jason Glaspey: And not necessarily like job offers, but just like, “Oh, there’s something there or there’s something there. Or I bet someone can make money doing that.” But I know that I no longer want to do things that I’m not naturally great at. I want to build my day around things that I love doing. And so how can I use my unique skill sets that I love exercising, in a way that helps people so much that I get money for it? And so what jobs align with that? What products align with that? And so that’s kind of led us to saying no to a lot of things.

Jason Glaspey: And then earlier this year… And also I’ve just gotten super easy to say no to great ideas. They’re everywhere. And so just because if they’re not right for me, I’m going to be miserable working on them. And part of that is getting to know who I am and trusting who I am, and trusting my instincts like, “Oh.” I heard about the FBA, Fulfilled By Amazon world seven years ago, six years ago. I looked into it and when I looked at the day-to-day I was like, “I hate doing every one of those tasks. All of those tasks, I am miserable in that situation.” And so I just walked away. And it took me forever to not feel like I was missing out. But I just recognized like, “Hey, someone’s awesome at that. Let them be awesome at that. I’m awesome at this other random stuff, so let me be awesome at that.”

Bjork Ostrom: How do you know what that is? Because I think a lot of people are trying to figure that out. And then also trying to figure out, how do I then create a job around then? Is it more of a gut like, “Hey, I’m doing this, I don’t enjoy it. I’m doing this, I do enjoy it.” I read a book a while ago called Designing Your Life. And they have this little thing where you write down what you did, and then it’s like a fuel gauge like how much did it take out of the gas tank? Versus like, were you full or empty when you did this? It’s kind of a way to go through that process that you’re talking about. What does that look for you, or have you been kind of creating and working for a long enough period where you kind of know what that is?

Jason Glaspey: Yeah. One of the ways that helps is to know what are the projects that I just burned out on so fast? And when I was just like, staring at email open rates and trying to optimize subject lines, and then like, “Okay. Well, if that’s optimized, then what’s the next step in the optimization chain? Okay. So hey, write five new emails and see which one gets a slightly…” To me, there’s an interesting part of that, but it becomes soul crushing after a short trip. And so I feel like, I know how to do that actually. I’m pretty good at doing that and I’ve done it professionally for a few years. But I don’t enjoy it. I’m not pumped.

Jason Glaspey: And so now I know that, hey, when that time comes for my next thing, when I need to write an email, I know how to do it. I don’t have to hire that out. And I’m going to do it at a pace that I’m comfortable with, and I’m going to do it with my style that I enjoy writing. And if that means that I don’t have as many customers, that’s okay, because I’m happy to get paid less to spend my time doing the things that I like doing.

Bjork Ostrom: Yeah. There’s that it’s like, I roll at this point, but that idea of the conversation between a fisherman and a businessman who’s like… And essentially, to not have to tell the entire story, the business guy is like, “Hey, why don’t you buy a big boat and make more money doing this?” And eventually he comes to find out that, you would do all of that in order to then be able to fish every day? The guy is like, “I’m doing it.” It might not be at scale, but essentially, what I hear you saying is, how do I move towards a reality where work doesn’t feel like work. And then, as long as you’re able to make ends meet, and provide for the things that you need to cover, that’s kind of it. You’re doing the things that you want to do every day, and you’re creating an income from it. But I think the hard piece-

Jason Glaspey: That’s the peak of success to me.

Bjork Ostrom: Yeah. But I think the hard piece that’s easy to gloss over is the make money from it.

Jason Glaspey: I have thoughts on that.

Bjork Ostrom: How do you make money on it?

Jason Glaspey: Yeah. One of the things is, it’s not easy. Everyone thinks that like, oh, after 20 years of building the skill sets, then it was easy. But you have to learn the skill sets, and you have to put in the time and you have to care, and you have to work hard at it and you have to pay attention. And you just don’t like anything. If you want to be a great pianist, you have to spend time in front of the piano. But also, I think that one of the things is that fisherman… So by the way, that is absolutely one of my favorite stories. I want to have the whole thing tattooed on my back. It’s amazing. I live and breathe that story, because one of the things no one thinks about is if you do the route and you buy the bigger boat, and you get all the stuff, then you have a sweet mansion. And you have people cooking and people cleaning and a gardener and a guy for your pool. And your life is polished and simple. Maybe. Right?

Jason Glaspey: And I think that’s what people think of that they need to reach when they reach the, “I’ve made it.” One of the big things, so we had like I said, a pretty good financial event seven years ago, and then I spent seven years trying to figure out WTF I do next. And there’s definitely been a moment in there where my wife and I, we were basically broke. I mean, we don’t need to get in the details but we’d spent our opportunity money. We were doing gig work again, I was consulting, I wasn’t really enjoying it. And we were starting to go into debt because when my clients wasn’t paying on time, and like fully, fully evaporated money. We were so far from like the, “We can do anything.”

Jason Glaspey: And I mentioned that only to say that we’re building our next business under very meager resources. We are not paying for everything, we’re not hiring everything out. But we’re also significantly lowering what our costs to live are. I’m happy to have a car with 180,000 miles. I’m happy to have a modest house that I love, but by no means would get anyone excited. We live in Mexico, like I’ve said, and most of the year, and we live in a eco-village community that’s off grid with solar. And we can totally reduce our cost, but we also say no to so many things. We don’t travel as much as we used to, we don’t buy nearly anything compared to how much Amazon used to come to my house.

Jason Glaspey: And it’s like, man, I can totally make more to have more, but I have never been happier when I had more. And I’ve found that after I was broke a second time, I am so much happier when I’m not managing stuff, when I’m not trying to earn stuff, when I’m not worried about what I have, and the ego balance of it. So we’re big fans of like spend less, make less, and spend the meat of your life doing just whatever the hell brings you fulfillment and supports the people around you. And if I decide I want to make more, we’ll figure out how to make more. But first and foremost, we’re not optimizing for wealth and accumulation, we’re optimizing for pure love of…

Jason Glaspey: And that means my wife, she’s super tense about money, so we have to have a savings plan involved. So we have to make enough that we are putting money away for savings, we’re not being irresponsible. But we’re picking the lowest amount possible and choosing to forego things so that we can say yes to our life.

Bjork Ostrom: Yeah. It’s almost like Mr. Money Mustache meets startup building, like those two things at the same time like, “Hey, I don’t want to…” It’s not like you’re thinking about it is, how do we live a retired life, in the same way that maybe some of the people from the FIRE community would, which we did a podcast interview on that. We’ll link to that in the show notes for somebody from the FIRE community. But like, could you talk about that? Are you familiar with Mr. Money Mustache, and does any of your thinking on how you live life come from some of the concepts that align with what he talks about?

Jason Glaspey: Yeah, totally. I remember when I first started reading his blog a couple of years ago, I went through a whole series of like, “This guy is incredible. This guy is a freak. This guy is cool, but not my game. I could probably learn something from this guy. I just did learn something from this guy.” I don’t want to read this guy’s blog all the time though. Like, he’s really thoughtful, it’s all very good, but it’s long. And it’s like, “Oh, man. I can’t go into that emotion every time I see one of his posts.” But every once in a while, I’ll check him out and I’m just inspired. And as the couple of years have went on, I have found myself coming into alignment with him more and more.

Jason Glaspey: And also just, it’s nice having him as a, I’m not crazy. Someone else is leading this charge, and is kind of waving the flag and I can at least look over and be like, “Hey, I’m saying no to a bunch of arch modern cultures ideals. I’m saying no to a lot of those.” And he’s just a strong presence that can remind me and my family that like, “Nope, totally normal actually. I dig what this guy says, I dig his values, I dig the way he’s trying to find solutions to life.” And I think about like, he doesn’t want to have a gym membership, so he does the physical labor around his house. And it’s like, “Yeah, I don’t have to pay for the physical labor, I don’t have to pay for the gym membership, and I don’t have to pay for a handyman.”

Jason Glaspey: I think one of the big shifts for me with that type of mindset was to really get enough time away from the computer for an extended period of time to help me see, “Oh, God, I hate being in front of a screen.” I’ve made my entire career based on the Internet, and I absolutely loathe sitting down at a computer anymore. I don’t want to optimize any of the apps I used to optimize, I don’t want to have a to do list and super slick. I don’t want to be on the screen. One of the things that shifted was during the first lockdown of COVID last March, I was in this ego community and we just hold up, and this community and we were outside every day, the community was still really tight, and it just totally changed. We grow our on food and we have an amazing garden. And just my whole idea of like, you can live without needing to earn tons of money, and you can spend your time happy.

Bjork Ostrom: Yeah, yeah. Right.

Jason Glaspey: Amazing.

Bjork Ostrom: Yes. I think of this term ramen profitability that comes from Paul Graham, but it’s kind of like, he uses that as like, you got to stay this way for as long as possible, so that you can grow your startup really big and essentially survive in order to then scale. It’s like, or you could just stay there, and to your point, optimize around other things. So the goal then becomes, or the currency is not actual cash or dollars, but rather autonomy, time, or to your point like happiness.

Bjork Ostrom: I think the hard thing with that is we don’t quantify it. If we walked around with an app that we would pull up, we could check our bank account, and it would show us our trending happiness for the past 30 days. Or if we had a score above our heads, and we could see how happy everybody else is, and you walk by and you’re like, “Wow. That person is really happy. How do I become happy like that person?” Or whatever word you want to use for it, happy, joy, content. I think you’d find people optimizing more for it. I’m curious to know, how do you continually nudge yourself towards that, and away from the thing that is such a strong poll, which is like metrics, numbers, growth, scale, whatever that might be, especially when you look at things online?

Bjork Ostrom: Personal improvement, you can always get a little bit better. It’s a lot of what we talk about. How do you get a tiny bit better every day forever? I think that applies not only to business, but also how you operate personally. And we all want to be getting better in regards to our investment in our family, our investment in ourselves, and just how generally happy we are. But how do you nudge yourself towards that over time? What does that look and not get drawn into kind of the strong poll of the traditional success?

Jason Glaspey: Yeah. I think one is a long commitment to change. You can identify like, “Hey, that’s the direction I want to go. I’m probably going to wake up tomorrow and have other feelings, so I’m going to have to be committed to like, hey, I’m going to slowly change parts of my life that take me away from that.” One way is start deleting people on social media who pull you the wrong direction. Another easy solution, yeah. Another is, cancel your prime membership. You don’t need to buy, you have enough. Remind yourself, what metric are you serving and what is the purpose of that purchase? Is it improving your true life, or is it just quickly solving a problem, an inconvenience or whatever?

Jason Glaspey: Also, I think a big thing for me has been working with my wife really closely. She’s a graphic designer, so we’re super in tide, and we’re both integral parts of this thing that we’re building. And talking to her often, reminding ourselves what our values are. When I’m not checking my bank account every day, but I’m checking like, “Hey, honey. How are you doing? How are you feeling? Do you feel confident in our decisions?” We kind of learned from the Basecamp, six week build cycles.

Bjork Ostrom: Yeah. Shape Up?

Jason Glaspey: Shape Up, yeah. So we’re kind of doing six week cycles within our family and just being like, “Hey, for the next six weeks, this is what we’re working on. On the business, on our family, and this. We’re not answering any other big questions other than these.” We’re not answering, “Should we do this or that?” We’re not trying to solve for this or that. We’re efficiently trying to optimize our whole lives. We identify, “This is what we’re working on right now.” And when big problems come up, we’re like, “No, no. Not what I’m trying to solve right now.” And it’s useful both from work and life. And it allows you to say, “These decisions are locked in. I’m working on these things right now.” And then that’s your focus every day. You don’t have to worry about some of the others.

Bjork Ostrom: What if somebody hears that and they’re like, “Gosh. I’m interested in pursuing a similar thing. How do you do that?” What does the unraveling and then rebuilding process look like? And what advice would you give to somebody who wants to change what they’re optimizing?

Jason Glaspey: Yeah. One, I’d ask look for the people who are the partners in your lives. It might be a spouse, it might be a brother. It doesn’t matter. Who are the people that you’re doing life with, and how can you work with them to achieve your goals collectively? And again, like, “Hey, I want to make $5,000 a month, so I can live this lifestyle.” Well, who’s with you on that? And it doesn’t mean they have to be your actual partner, but like, are you just stating something into the ether end, defining it as a goal? And something that we talk about a lot is, what does it look like to perfectly be executing our plan right now? And how far are we from that?

Jason Glaspey: We acknowledge that we’re never going to go through all the steps without making mistakes, that there’s like go two, three steps forward, one or two and a half steps back, and then seven steps forward, and then left turn 80%. We understand that, and we don’t expect to remove that. But we do ask, “Okay. What does it look like to be perfectly executing our plan, and what are we just totally missing on? And how do we get to there?” Those force you to not look at the daily circumstances, but look at your goals. And they force you to define what you want.

Jason Glaspey: It’s really easy to not actually define what we want, and just say it’s something that’s over there. It looks kind of like that. “Oh, he’s got it. I kind of want his version.” “Oh, she’s got it. I kind of want her version.” And like you were kind of saying, “Oh, this or oh, that,” whenever you see something. But when you know what you want, and it’s totally locked in, you’re not tempted to look at the numbers that don’t help you get there.

Bjork Ostrom: Right. Yeah, Lindsay and I have talked about this idea, in this season of life, which is especially true for us, but the idea of North-ish. And what I heard you talking a little bit about is like, you have a clear picture of where you want to be, and you kind of zigzag to get there. But you’re kind of generally going north-ish. And there’s been a couple of conversations that we’ve had lately, where we’re like, “Hey, north-ish.” Like generally headed in the right direction, it’s not perfect and it’s a difficult journey, but we’re generally going there. But you need to know where there is like, what does that actually look like? Which I heard you saying, which I think is really great. What is the thing that you’re working on? You’ve talked about that a little bit now, but I’d be curious to know what your main focus is, and even kind of day-to-day, what that looks like now as you’re building your ideal day.

Jason Glaspey: Yeah. Two or three years ago, I was working with an amazing director of a private school here in Mexico. It’s an international school, it’s awesome, and this guy was just a savant when it comes to children and relationships. And I learned a lot from him. At the time, I just really acknowledged that as families, we have single family homes and we have completely lost tradition with how to do just some of the simplest things as a family, and ancestral knowledge of, “Oh, don’t do that or do that.” Well at the same time, our world has changed so dramatically that we can’t go to some of our older relatives and ask for help. Because grandma doesn’t know the right amount of time for my kids to watch the iPad. I can’t go to her and be like, “Grandma, how do I solve this really tough problem?”

Jason Glaspey: And then to also say, but we also don’t live anywhere near our family, so even the common things we have solved, we don’t have the benefit of their sharing their knowledge. So we just kind of recognize like, “Hey, what if we could make parenting lives just a little bit easier by providing some sort of data or content or something?” And we’re very open about what that looked like and we’ve explored a bunch of different versions. And then, when COVID fully hit, we just put it completely on hold. And now, as of 2021, we’ve reopened this idea and we’re focused 100% on a potty training product.

Bjork Ostrom: Nice. Before we press record, I was like, that’s the season we’re going into, so this is going to be a podcast interview/early beta user sign up.

Jason Glaspey: Yes. What we just noticed was, I did some looking in parenting forums, and I just saw a recurrence of people asking for really direct, honest, sincere questions about potty training that showed that they didn’t have anyone else to really talk to. And one, it just breaks my heart like, how are we failing our families this much by not providing resources? And the other hand is the only real resources I found other than maybe 400 word articles were 300 page books. And as my wife said, every major milestone is another parenting book you’re supposed to read, and she’s like, “We just don’t got it.” And so just being super inspired by PaleoPlan, like how can we do research to solve one problem and let it scale? Babies need to potty train is not going away, and there’s 2 to 3 million new babies born a year, so there should be lots of babies that need to potty train.

Jason Glaspey: So we identified just that market, but then we identified just no one has made a just great solution to helping a parent. And then what’s the empathy for that parent? They don’t want to look at a desktop site, they want to look at a wonderfully designed mobile experience. And they’re tired, and it’s probably late at night, so they don’t want long, wordy articles that are hard to understand, and really complicated frameworks. And really it’s like, hey, how do you take all that understanding of parenting, all the fatigue, the worry, the guilt, the shame, all the places it comes from, and then purify the content they need in a way that is perfect for them?

Jason Glaspey: And we have some ways that we’re trying to do that. Some of it is heavy reliance on summations. You do not need to read five pages about rewards, most parents need to read three paragraphs. But then there’s that kind of wire cutter style. Some parents need to know more, or they want to check your work, or they kind of want to see how a sausage is made. And so then you do have that information, you do go deep, but you provide lots of ways for people to access that content to get straight to the part they need and back out. And as someone who’s built websites for 20 years, my wife is a graphic designer, we think about this stuff all the time. It’s like that’s what we know how to do. We know how to take complex information and make it fun and easy to…

Bjork Ostrom: … to look good, and yeah. So I’m interested, as we kind of come to the end here, I’m interested to hear, what are the tools you’re using to build that? I know that you’re always kind of talking about beta user of software, but that’s something that you’re always aware of, and I feel like you’re really connected in the startup software community and know tools that work really well to build products online. So what does that look like for you?

Jason Glaspey: I’m trying my hardest to keep things simple. In the past, I’d be like, “Oh, here’s a cool this I can use for that.”

Bjork Ostrom: This app here to connect to… Like when they pull it up it changes the temperature. Yeah.

Jason Glaspey: And now I’m trying to be like, most of that stuff doesn’t help the customer. In the end, what helps the customer is super fast access, super fascinating websites, really clean navigation. So we’re just using Webflow. I’ve gotten to know Webflow really well. I’m proficient at it. I’m finally at a point where I can write anything I want. I can create almost anything my wife and I can imagine, without needing outside help.

Bjork Ostrom: Can you talk about what Webflow is? A lot of people would be familiar with WordPress, but how’s Webflow different?

Jason Glaspey: Webflow is like if WordPress was made now. But it’s without a blogging paradigm, but more of just like, “Hey, how do you help people build websites that don’t need to know every ounce of code?” So it’s a no code tool. It uses a very modern interface to give you the ability to use basic CSS commands without having to know syntax. And you can say like, “Center that,” and it centers, and you don’t have to write. And if you know the structure of code, but don’t want to type it all out, it’s perfect. It’s getting to the point where you don’t even really have to know the structure of code, but it will help. And it’s very heavily focused on people who want to create compelling design. So it makes unique, and what would be very difficult in WordPress design-wise is much, much faster and simpler in Webflow, and you don’t need to have any experts or funky plugins for a lot of things.

Bjork Ostrom: Right. Right. That makes a lot of sense. Could be great in your case where you’re wanting to create a really beautiful, easy to use experience. I haven’t spent a lot of time with it, probably early stage for anybody who’s building and wanting to optimize for search engine optimization for recipe type content. But if you have a recipe, or if you have maybe a product you’re promoting, something you’re selling, more like branded type stuff.

Jason Glaspey: Yeah. Marketing sites. It’s amazing for marketing sites.

Bjork Ostrom: Yeah, that makes sense. So last question that I want to ask you that we could do a deep dive on in another podcast, because it’s probably a big question. But I’ve just noticed, one of the things that’s fun about being connected with you is noticing all the different places that you’re connected around the different communities I’m a part of. I was just looking on Twitter earlier today, Justin, who’s somebody we’re connected with is working on an app called Upfocus. And then you tweeted about 15 years ago, the first check that you ever got with a comma in it was working with Justin on something. I’m like, “Wait, Jason knows Justin.”

Bjork Ostrom: You introduced us to Katie who works on the WP Tasty team and leads all the work over there with the WP Tasty team. Maybe it’s just by chance that you got connected in here, and then suddenly you’re kind of in that little circle, but it feels like you’re a really good connector. For people who also want to be good at connecting and getting connected, how do you do that? Because you’re good at it. And I think it’s important for people to know how to do that.

Jason Glaspey: Well, that’s a super nice compliment, I appreciate it. A lot of it was I got on the Internet 20, 25 years ago, when it was kind of young, and I found the other people who were on the Internet in Portland at the time and got to know them. For Justin, for instance though, him and I actually went to ad school together in college. We started advertising together. So I really have known him for at least 20 years. And then but also, I’ve been lucky to just there’s been really great people around that I’ve been in the right spot to get to know, and then their careers have just done awesome things. And so I after 25 years of being in the industry, you start to know the people, and the people who’ve done interesting things have been around long enough that I might have met them early then.

Jason Glaspey: I definitely would say that’s how I’m connected to Portland was I was just, there was a time when all of Portland had 100 to 200 tech folks that were in this little community. And if you were part of it back then, it didn’t take long to get to know all of the people. And then as Portland’s grown, it’s filled up as this really nice scene. But you know enough of the connectors in that because they were there early on also. Twitter has been like that for me. I was kind of early in Twitter, and just found like, “These are the guys to listen to.” And I was there early, so I got followed by a few of them. We made connections and now allow me to bounce around. And then hopefully trying to do work that matters, trying to do work that I’m proud of, and connecting myself with people who are also doing work that they’re proud of.

Jason Glaspey: There’s a lot of things I’ve said no to, that are about money or about other things. And I’ve tried to as much as I can lead towards things that I like doing, I’m proud of doing, and it allowed me to do my best work. And when I can do my best work, then that tends to introduce you to people who are trying to do the same. And not by any means have I always done great work, but it’s my hope.

Bjork Ostrom: I know that personally, I’ve benefited from it in multiple ways. And so a recorded thank you for the connections you’ve made. And also, I’m just grateful to be able to when I’m sorting contacts, be able to put you in the friend bucket. And I’ve learned a lot from you and have also made some great connections for the people in my life, so really appreciate all that you’ve done for us. Thanks for sharing your story, Jason, on the podcast, and excited to stay connected moving forward. If somebody wants to reach out and connect with you, best way to do that would be what?

Jason Glaspey: Twitter is a great way, or jasonglaspey. Mostly proudparents.com is where we’re going to be announcing our potty training. It’s Pooping on the Potty, the Online Academy. We’re going to be beta testing in about a month, and then launching it this summer. And also, I want to say to you, Bjork, I’ve had a chance to get to know you, and I consider you also a friend, so that’s reciprocated. But for all the listeners who hear Bjork and wonder like, “Can this guy really be this nice and thoughtful all the time?”, like for those that haven’t had the pleasure of meeting you, I want all the podcasters to know that he is easily one… Bjork is easily one of the most sincere, thoughtful, guys I know. And also one of the most amazing question askers. Which to me, implies that you actually care about the people that you’re talking to. You listen really well, you follow up on what they say instead of retorting. Your empathy and sincerity is always three feet in front of your body, and it’s amazing to interact with you.

Bjork Ostrom: Well, really appreciate. We’ll start to do opening clips on the podcast now. We’ll cut that one out, and we’ll just use that as the opening clip. We’ll just shine a light on it.

Jason Glaspey: Perfect.

Bjork Ostrom: No, really appreciate it, Jason. Thanks for coming on and sharing your story, and excited to stay connected moving forward.

Jason Glaspey: Absolute delight, man. Thank you and take care.

Bjork Ostrom: Thank you to Jason for coming on the podcast. Jason as always, really fun to talk to you. And one of the things I appreciate about a podcast episode like this is, it provides another lens, another way to look at things, and sometimes what can happen when we go heads down, when we’re working on the thing that we’re working on. We look at people who are doing similar things and we try and do what they’re doing. Or we have conversations with friends who are doing the same things as us, and we can get kind of microfocused on a really specific goal, which is good, but outside perspective and outside ideas, like the ones that Jason shared today are really, really helpful, and I always appreciate them.

Bjork Ostrom: So another big thank you to Jason for coming on today. And thank you to you podcast listener for tuning in. If you’re listening to this as a one-off episode, maybe you stumbled across it somehow when you were searching for a podcast to listen to, you can go ahead and subscribe to the Food Blogger Pro Podcast. All you have to do is just search for Food Blogger Pro in the podcast app that you use, and hit the subscribe button. It’ll make a big difference for us as we continue to grow this podcast, and hopefully have as bigger reach as possible as we continue to share this message of showing up and getting a tiny bit better every day for ever. Thanks for tuning in.

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