November 12, 2025

00:40:31

Ep 14 - Culture Shock

Ep 14 - Culture Shock
Offsite
Ep 14 - Culture Shock

Nov 12 2025 | 00:40:31

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Show Notes

Are you building a business that fits your personality or following someone else's playbook? 
 
Jordan Gal hosts Jon Ewalt, founder of Roaster Tools, a comprehensive ERP system built specifically for specialty coffee roasters. After selling his Portland coffee roastery, Jon dove into software development nine years ago and has been "playing catch up" ever since. Now based in San Miguel de Allende, Mexico, Jon discusses the challenges of building desktop software with long development cycles while prioritizing personal time alongside business growth. How do you balance sustainable business practices with ambitious goals? Jordan and Jon explore the reality of mid-40s entrepreneurship, the value of a tight-knit founder community, and why Jon chose to move his family to Mexico for immersion Spanish education. Their decade-long friendship offers insights into building businesses aligned with your personality rather than chasing hockey stick growth. 
 

In This Episode:  
(00:00) From Coffee Roaster to Software Founder 

(01:39) Why We Moved Our Families to Different Countries 

(04:23) The Immigrant Experience and Core Memories 

(09:30) Launching Too Early: Playing Catch Up for Nine Years 

(18:45) Building Desktop Software vs Web Apps 

(25:30) The Founder Mastermind That Predicted Our Paths 

(33:56) Mid-40s and the Question of What's Next 

(38:21) Moving Up the Abstraction Layer in Business 

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About the Show 

Jordan Gal, founder and CEO of Rosie AI, hosts the Offsite Podcast where he teams up with rotating entrepreneur friends to explore what's happening in their work and beyond. After successfully building and selling CartHook, Jordan now leads a VC-backed company while sharing candid insights about the realities of startup life. The show combines real-time business updates with deeper conversations about founder psychology, growth strategies, and the personal side of entrepreneurship that rarely gets discussed publicly. 

Resources: 
 
Jon Ewalt LinkedIn: https://www.linkedin.com/in/jonewalt/ 

Roaster Tools: https://www.roastertools.com/ 

Rosie AI: https://heyrosie.com/ 
 

Chapters

  • (00:00:00) - Off-Site Podcast: The Place of Work
  • (00:00:59) - Living as a Non-American in Mexico
  • (00:06:19) - How To Raise An Immigrant Child
  • (00:09:00) - How to Run a Coffee Company for 10 Years
  • (00:13:03) - Tyler and Jordan on Their Differences
  • (00:18:48) - Top Software Executives: How Do You Manage Your Team
  • (00:25:19) - Roaster Company's Big Features
  • (00:30:53) - Have You Had Any Negative Feedback From Your Partners?
  • (00:33:09) - A Slack Group For Old People
  • (00:38:52) - Have You Reached a Point Where You Can Exit Your Business?
  • (00:39:59) - A Taste of Mexican food
View Full Transcript

Episode Transcript

[00:00:00] Speaker A: My story was we ended up selling this roastery that we built in this cafe and we moved to Portland, had a little chunk of cash and I was like, I'm going to hire some smart developers. And we got to the point where we were able to launch. We won like a best new product award in our category at a coffee conference and we had a splash. And then there was all this reality of like, I don't know how to run a software company. I don't even know how to like serve these customers. Oh my God, I'm way over my head. And that's been my, like, I've been playing catch up now for nine years. [00:00:29] Speaker B: Welcome to the offsite podcast. I am your host, Jordan Gahl. This is where I team up with friends to catch up on our work and just as importantly, what's going on beyond the work. As always, this podcast is brought to you by Rosie, the AI powered phone answering service for small businesses. Hello and welcome back, everybody. Another episode of the off site podcast. Today I have my good friend John Ewalt. John, how's it going? [00:00:56] Speaker A: Good, Jordan, thanks for having me on. Absolutely. [00:00:59] Speaker B: So we need to set the stage a little bit here. So if you give me, give me a minute. John and I are close friends and our families are close friends. We lived in Portland at the same time for a long time and we had one of these very lucky situations where John and I match up, our wives match up, all three of our kids and the three of your kids match up. And we, yeah, we really loved spending time together. And then we left Portland at like, really the same time, like within a few months. [00:01:33] Speaker A: Yes. [00:01:34] Speaker B: I went to the boring Midwest near Chicago. And where did you go, John? [00:01:39] Speaker A: We moved to Mexico because. Why not? [00:01:43] Speaker B: Because you're a, you're a 25 year old digital nomad with no responsibilities. [00:01:46] Speaker A: Right. I wish, I wish we would have gone to Mexico City if that was the case. But we ended up in, in San Miguel de Allende, which is like a beautiful colonial city, like 175,000 people. It's, it's, it's great spot. [00:02:00] Speaker B: Yeah. With a lot of expats. So it's not like you're off somewhere completely remote. It's unique in that way where it's a very international city. Is that right? It is. [00:02:09] Speaker A: I mean it was just named like the travel and leisure is like best place to visit in the world, you know, like number one. Like it's, it's an amazing destination and so it draws a lot of expats. So there's a lot of amenities, and if you want to get by without speaking any Spanish, you can do that, you know? But as a family, one of the things we were trying to do was kind of leave. Leave Portland and go and challenge ourselves, I guess, and got to do something different. And we wanted all of our kids to learn Spanish, so we dove in, and we can still go to the supermarket that's super nice and get the things that we kind of want from the States. But then at the other time, it's like, we're walking through this colonial city with cobblestone streets. That's gorgeous. [00:02:50] Speaker B: So it's very, very unique. You and your family were very useful to my wife and I because whenever our kids complained about the transition from Portland and the schools there and to Chicago, and whenever they were like, it's so hard. I don't have any friends, we'd be like, yeah, but don't forget the Ewals are doing this in a different language. Okay. And that's much harder. [00:03:14] Speaker A: And we literally had no preparation for our kids. We. We threw them into their first day of school, and I think it was probably two weeks before my. My youngest son knew how to ask, like, to go to the bathroom, like, where the bathroom was, you know, like. And he. He got brought into the principal the first day. I mean, there's all these stories that came out not then, but like, six and 12 and 18 months later where they're like, oh, yeah, this happened, and we had no clue. [00:03:38] Speaker B: So. [00:03:38] Speaker A: So we thought we were being protective and good parents, and we just kind of threw them to the wolves. And now they're amazing. They're basically fluent in Spanish. So, yeah, it feels like it would. [00:03:49] Speaker B: Be one of these experiences where the payoff is as high as the difficulty is low. Yeah, you go in and it's really, really hard, but you get this huge reward in character and challenge and experience. [00:04:06] Speaker A: Definitely, definitely. And it's, you know, like, each kid has grown in different ways. And, like, that's been. That's been exciting. And, like, taking seven or eight classes in Spanish, you know, like, physics and math and all of these things, it's like, it's hard enough, like, in your negative language, let alone. [00:04:21] Speaker B: Right, that's right. [00:04:23] Speaker A: Yeah. [00:04:23] Speaker B: I can't. I can't help but think about my experience as an immigrant, being six years old, going to first grade and being like, where am I? What is happening? How. How did I end up here? And, you know, it's a very intense experience. I was going to say, like, negative or positive. It's kind of just intense. [00:04:42] Speaker A: Yeah. [00:04:42] Speaker B: On both the negative and the positive, like, you become very independent, but there's like some fear involved and some intimidation and then you have to go through these challenges of speaking up and trying to overcome. I, I still, I still remember the individual time that one girl in my first good class made fun of me because I couldn't speak properly. It was like, it's a long time ago, bro. You know, but you still, you remember. [00:05:07] Speaker A: Yep. Core memories. [00:05:09] Speaker B: Cor. I remember going to the supermarket and buying a, a lunchbox and it had some pink on it and I didn't know that's like, not allowed for six year old boys in Long Island. And so I remember going to the cafeteria the next day and the other boys at the table being like, got a pink lunchbox, bro. Like, what are you doing? I was like, oh my God. I, I didn't, I didn't know. I didn't know what I did wrong. Yeah. [00:05:34] Speaker A: Yeah. [00:05:34] Speaker B: So hopefully your kids have, you know, the other side also. [00:05:38] Speaker A: I think so. But I think there's also like, they've, they've said some stuff that like, they probably look back and they're the moments where like, they regret what they did. People are laughing at them. Like, there's all of that as well. And, and now we're like, yeah, you guys are great. Like you could. What other country should we go. Go. Go live in? You know? [00:05:54] Speaker B: Yeah. I mean, I guess that, that what it does is it, it changes them and it forces their character to be tested and that's almost always ends up as a positive thing. Even if it, there's pain that you go through to get there. [00:06:12] Speaker A: Definitely, definitely. It's, you know, it's funny because, like, I'm an American and I kind of think myself is like, you know, I'm an American and. But I'm an immigrant right now in a different country. And it also has reframed. Like my kids are immigrants basically growing up, learning a second language, learning a second culture. They know more about like Mexican states than they do US States at this point. And so there's, there's like this, like. I know whatever we've done for better or worse is going to shape their worldview for the rest of their lives. Yeah. And their perspective. [00:06:45] Speaker B: Yeah. Right. We're, we're like caretakers, literally until they're 18 and then they go off. [00:06:51] Speaker A: Yeah. [00:06:51] Speaker B: And a lot of it is just guardrails. Like you're not taking the test for them, you're not making the decisions for them around who to hang out with his friends. You're kind of hoping for the best and providing guidance and some advisory. You're not leading that that's them. But what you want when they come out is a self assured person who's confident in themselves that could go out and take on challenges and believe in themselves. All these other things, it's kind of like the best you can do. Besides that they choose the direction and what they want to focus on and where they want to live and whatever else the danger or what feels like a risk in providing an extremely stable environment, safe environment, is that there aren't. There aren't many challenges on the way. You know, So I look at my kids and I'm like, you got it pretty easy. We kind of have to throw some hurdles your way on purpose to do different things and travel different places. Otherwise it's just this cushy little, you know, guardrail bumper bowling thing where if you get shot out the other side without any going through any challenges, that, that's kind of a bigger worry. [00:07:56] Speaker A: I'm starting to think about colleges right now for my oldest and it's like it's still a few years away, but when you read about the way the colleges are set up today, it's kind of made for the bumper kids to be. To transition successfully because it's. The dorms are nicer than we were. You never had like everything's up landing. Yeah. I'm like, I want my kids to go and have to go to the place where there's a bathroom that has 15 different stalls and you have to interact with everybody. It's not like a private experience. You know, I want them to have this. Yes. Communal like thing. Like I don't want them. Right. [00:08:31] Speaker B: Go, go rub shoulders with people who are very different from you and deal with it and learn from. [00:08:35] Speaker A: Exactly. Yeah. And get pissed when somebody's like taking too long to shower and like, you know, like all of that. [00:08:41] Speaker B: Yes, yes, that's right. [00:08:43] Speaker A: I mean we have, both of us have three kids, right. So I think we have some of those experiences built in with like the number of people and there's always, there's always a finite number of resources in a family. And so there's going to be those like, you know, why did she use the bathroom right then? Or like, you know, all of that stuff's gonna happen. [00:08:58] Speaker B: But yeah. [00:09:00] Speaker A: Cool. [00:09:00] Speaker B: Well, while you've been down there, you, you have been running the same company from before you moved to Mexico and now. So you, you really took advantage of being Able to be remote. And how's that going? How many years in are you now? And I mean, tell us about Roaster tools. [00:09:18] Speaker A: Yeah, so I've been running this since, like, 2016. So next year is going to be my 10th anniversary, which is, like, crazy to say. I am. I am like that. Like the slow ramp of depth SaaS graph. Like, I am that person that's been walking that path just little by Little for 10 years. So started in Portland. My background is I was a coffee roaster. And then I was like, I could do these tools better so that we don't have to do all these things manually. And I never knew anything about software. So, like, literally, my journey begins kind of actually when we met, because. [00:09:50] Speaker B: That's right. That's right. I remember you being like, I think I'm just going to learn the code myself. And I was like, what, bro? [00:09:56] Speaker A: And I had no idea how hard that was. And now I'm paying the price because, like, we're. We're nine years into a code base that's got tech debt and all this other stuff that just because I had to hire contractors, right? Like, my. My story was we. We ended up selling this roastery that we built in this cafe, and we moved to Portland, had a little chunk of cash, and I was like, I'm going to hire some smart developers. And we got to the point where we were able to launch. We won, like, a best new product award in our category at a coffee conference, and we had a splash. And then there was all this reality of I don't know how to run a software company. I don't even know how to serve these customers. Oh, my God, I'm way over my head. And that's been my. I've been playing catch up now for nine years of, you know, just a little by little. And. But that conference that I won that award at, I think it was like, I don't remember the order, but I either won the award on, like, a Wednesday, and the previous week I'd gone to microconf for the first time or something like that. There was some relationship where it's like, okay, these two conferences are always kind of back to back. [00:10:59] Speaker B: And so software in the coffee world, those two parts. [00:11:03] Speaker A: And so I feel like that was like me writing notes furiously as I'm going to microconf and trying to figure out how to do this thing. And I've been listening to podcasts and. [00:11:12] Speaker B: Yeah, so what. What. What I'm hearing is the. The forced learning curve that in many ways, you Know, a lot of us went through around the same time. You know, I, I moved to Portland. Was it 2014? Something like that. [00:11:26] Speaker A: Okay. [00:11:26] Speaker B: And then I remember going to the microcon. Was it. I don't know if it was a meetup first. I think maybe it was microconf, the conference first. And then when we were there, we were like, oh, my God, there's like 25 of us from Portland. Maybe we should get together back in town. And then we started going to lunches. And that's how we first got to know each other. And the guys that we still talk to in Slack every day now. And many of us went through that learning curve. You and I, I think, were behind the curve compared with Jared, who was a developer. Ruben, who knows everything. Right. [00:12:02] Speaker A: He's the Godfather. That's. [00:12:05] Speaker B: That's, that's right. So that like all of us had no choice but to learn all of these individual parts. It's similar. I came from the E commerce world and I was like, oh, I know what an E commerce owner needs, so I'm going to build software for them. And you were coming from the coffee world, like, okay, I know managing and roasting and planning isn't done right, so I'm going to build a solution for that. So both of us kind of built a solution for our previous jobs, our previous endeavors, and then neither of us had a clue what we were doing. And then we would learn and learn and apply and learn and make mistakes and try to hire and try to raise money. And like, yes, it was a very similar parallel path. [00:12:47] Speaker A: Yeah, we had the years that we were in, we worked together where we were, you know, like, working in like a co. Working space. I mean, there's been so many iterations of our, like, watching people that we admire and we're like, oh, my gosh, look at that. You're like, yes, it's. Yes, yes, yes. Yeah, we. [00:13:03] Speaker B: We've had some lightning strikes near us, you know, that we wish would hit us. Where's my lightning? I'm ready. I'm ready for my lightning. I'm very happy for your lightning. But also, can you share? Yeah. [00:13:14] Speaker A: Can you just give me, like, can I just touch your hand while that happens? Because. Yeah. [00:13:18] Speaker B: But I think you and I have taken pretty different. You took a more patient approach and I was less patient. And it sometimes worked and sometimes didn't work for me. And at the same time, we just kind of watch each other like, well, I wouldn't do it your way, but that looks pretty good sometimes. And then the Other way it would come back. [00:13:35] Speaker A: Yeah. [00:13:35] Speaker B: So John saw the whole car hook roller coaster of starting very small and then, you know, blowing up super fast and getting crushed by Shopify, and you were kind of just chugging along, just steady. [00:13:48] Speaker A: You know, there's a lot of times where I've looked at what you've done, and I've been like, I've asked myself the question, does Jordan get it more than I do? Because, like, you have done, you know, it seems like you're always pushing that edge of getting things done. And it's something I've always admired because it's like maybe I've kind of, like, stayed in my lane a little bit too much, you know, like, as I look back at 10 years of history, there's always been that, like, are there some opportunities that I missed because I wasn't pushing things fast enough? And I think that this is what Rosie's doing really well is like, you found waves that you're not just like, you know, I'm playing in the small pond where there's just a ripple. Like, there's. There's nothing else happening here except for, you know, there's. There's a kind of finite number of coffee roasters. It's what I've known as, like, a. My past history. And then, you know, you've. You've kind of like, left from one pond to another pond to a bigger, like, ocean at this point, you know, and, yeah, it's. [00:14:40] Speaker B: And all the pros and cons that go with it because the competition is very different and the familiarity in the market and people getting to know you and that compounding benefit and advantage of being in the same place for a long time. So it's really been like a study in these micro decisions and all the pros and cons that come out of it, because at times I've looked smart by taking more risk and being more aggressive, and times I've looked stupid for those decisions. So generally, it's kind of like a question mark on I. I guess you gotta just follow your personality and gut on what you think is right there. There is not. There's not one path that's obviously better or worse. And if either of us had had a lightning strike, and I don't know if we're being too vague on this, by lightning strike, I mean like a great exit, an amazing outcome, something like that. I don't know if either of us could have looked back and said, oh, well, clearly I did the right thing and going slow and steady was the right Move or going super risky is the right. Was kind of like, all right, there's some surface area, some luck. [00:15:43] Speaker A: And I think it's also like that personality part. It's like when I look at, like, the things when we talk, and it's like, oh, yeah, you know, Jordan, you did this. You talked to this person. And it was like three layers down. There's, like three conversations that led to something happening. That's your personality. Like, you're gonna be the person that's gonna follow those conversations. And so that's gonna be, like, a natural outcome, I think, of, like, what your businesses are gonna do. And I'm more of an introverted kind of. Like, I love chatting with people one on one, but I'm not gonna be the guy that's probably gonna seek out that next conversation. And so. But I'm also gonna be really probably. I think I'm decent at product and I'm decent now at the tech side, and those are my skills or those are gonna be my foundations. [00:16:23] Speaker B: Right, right. And I never developed those. Yep, yep. That's right. What is cool about software and business in general? We constantly have the same issues, though. Constantly have the same questions, same problems, you know, same problems that we're coming to Ruben with, asking him to help us with. So. So that dad did a week. Yeah. Yeah. [00:16:46] Speaker A: Yes. [00:16:47] Speaker B: So John and I are in a slack group with Ruben, Gomez and Jared and a few of the friends. And it's kind of like this repository of, like, when I'm facing a problem and I'm noodling it on my own. And then I remember, oh, I have people I can go to. That. That's where I go. I think I just did it yesterday. What we talk about. Oh, I was talking about us basically coming to the realization that we can't run our product and development process the same way anymore. [00:17:17] Speaker A: Yeah. [00:17:18] Speaker B: We very purposely leaned towards speed and were okay with mistakes because we thought speed is the only thing that mattered. And then it resulted in more of a messy process and. And. And slowing down instead of speeding up now that we're one year in and more mature and have different issues. And now we kind of are going from this very waterfall, just grab the next thing at the prioritized list to sprints and a little sprint planning. And we're going to try not to release all at the end of the sprint. We don't think that's necessary. So I know you. You've developed this product skill over the last few years also because. Because you have no choice. As soon as you're not developing everything yourself, you need to process. [00:18:02] Speaker A: Well, it's funny because I actually thought that I did a decent job at this. And then my wife joined the company a couple years ago and she doesn't let me get away with like basically my bs, okay. And as wives and good partners do. And so, and we've had this come like, you know, like this reality moment where like, oh shit, I'm not good at this or I'm not, I'm not, I'm good at this. But I'm like, I'm not good at the process part to get it. The result we need when we have, when we're processing payments and like some of these things that are like these, you can't mess up the way that we did maybe two years ago. And so even I, who I think I'm good about like knowing what the product should do. I'm not necessarily good about the product process, but we're getting a lot better right now. So actually I was kind of curious to dive in because how are you prioritizing? How are you actually making decisions? Because you have now more surface area, more expectations, you have quite a few customers as well. And so there's gotta be this pull in so many different areas. How do you balance strategic versus what your customers are asking for versus the tech debt that, you know, everybody builds up like, yeah, how do you manage all. [00:19:13] Speaker B: That's right. Yeah, we, we. So we had this conversation at all hands on Wednesday two weeks ago. I think I talked about it on the previous episode. We kind of had a, a very difficult conversation internally around things not working properly and what do we need to do and, and how do we, how do we maintain the speed and scrappy nature and not too much process? But how do we, how do we make things better? There's in some ways there's over management and we see over management in the follow ups. Hey, did this get done? Hey, where are we on this? Like that's a bad sign. So when we started to get too much of that and then if you do that too often, then the people, especially the go to market, going to the developers and saying, hey, hey, where are we on this? Once you do that too many. Yeah, once you do it too many times, it erodes the trust and the relationships and then sometimes then things get kooky and you don't know they're getting kooky because the person's not even going to the developer and following up because they've almost like given up on it. And then at the same time, the developer is just like working all day and trying to solve things all day. And then a few weeks later they hear back like, well, you know, you didn't get back to me on this thing. So I've kind of like, just dropped it. And they're like, but I'm, I'm working all day. So we kind of had. Everyone was right and everyone was wrong all at the same time. Everyone was working very hard, but everyone's frustrated. But like, all these different things. And it became pretty obvious that that's a management problem, that's an us problem. Leadership, that's not the team. [00:20:43] Speaker A: And once you have those, I don't know if it's got like. And I, I say this with love. If. Which I, I'm sure my, my wife will listen to this, which, you know, like the, the snide remarks where you're like, well, we know that that's going to ship in four weeks. And I said one, you know, like, it's like all of the, like, like the kind of, hey, like, expectations are not quite what I, I say what I think I'm gonna take. But then it's, you know, when I talk with. We have one other developer on the team, and I'm like, hey, can we get this? The answer is always yes, but. And the buts are all the things that we do during the day. Yeah. All valued. Yeah, exactly. And it's like, well, and one of the realizations that we've had is that we are doing so many little tasks throughout the day that don't get tracked or don't get bus. There's no visibility into them. And so we've been starting to throw those into linear more. So like, even if there's like a, if there's like an ongoing task or if there's one that's like, we're doing a migration for, for somebody from X to Y, and we know that we need to schedule that for next Wednesday. And so rather than that just being like a slack, you know, request and buried in the long list of things that are happening, we're putting it into linear so that when we look at our current cycle, that's included. It's taken into account. [00:21:51] Speaker B: Right? Yeah. [00:21:52] Speaker A: Because, like, yeah, so that was, that was a big realization for us, was like, we can't have things hidden otherwise expectations are always going to be thrown off. [00:22:00] Speaker B: Yes. So not coincidentally, a lot of our conversation centered around when something leaves slack and goes into linear. Okay, why? And why. [00:22:12] Speaker A: What did you decide? [00:22:14] Speaker B: When does it. Yeah, it's really, really hard, actually. So, like, when does it rise up to the level of, oh, you got to put that linear, make, make it a task, give it a quick little estimate, something so the product manager can go into linear and understand what the developers are working on and what's on their plate. Because we found ourselves too often with the product manager looking at linear and saying, how come things aren't getting done? You don't have that much on your plate. But then you talk to the developer and they're like, I'm working 12 hour days. [00:22:42] Speaker A: Yeah. Spinning plates like left and right. [00:22:45] Speaker B: Yes, that's right. One of the first things we did is we put developers on shift for support. Because what we found is that the developers really want to help and they're also the right people to help. Like if you just release this feature or if someone, I mean, an AI product is real weird. It's, it's just like other software, but there's less visibility into what your code, how your code impacts the resulting AI, Right. [00:23:15] Speaker A: So you're like, it's a black box in a black box. [00:23:18] Speaker B: It is a bit of a black box. And the testing suites aren't there and the automated testing doesn't work the same way. And imagine writing code and imagine getting a support issue where Rosie's interrupting too much and saying, okay, got it, and then going into the code and saying, all right, let me, let me adjust this prompt sensitivity, this interruption node, whatever else, and then being like, okay, I, I don't know, I don't know how to test if it's good or not. And so the only thing to really do is to just pay attention to support and see if, see if there are as many complaints about it because no one's going to write it. Just so you know she's not interrupting. Things are great now, like, that's not a support ticket. That happens. And so what, what, it trained our developers to just keep an eye on support tickets and want to address things quickly. But then, then you have multiple engineers looking at support for hours a day. It's not that they're just staring at it, it's just that it interrupts you. [00:24:12] Speaker A: That context switch is so hard for somebody who's trying to do deep work or should be doing deep work. And then they're getting like pulled into these little microaggressions almost, and they're. And I have to imagine even that you're like, okay, so at the end of the day I got 15 requests or 15 different things that are complaining about maybe 15 different little tweaks that could be happening to our AI settings. How do you decide what to change? Because that seems like it'd be almost impossible to know. [00:24:38] Speaker B: Like, I mean, it's hard and the LLM doesn't always do what you tell it to. So if you change your prompt, it doesn't necessarily mean the LLM will actually listen. So. [00:24:47] Speaker A: Okay, so. [00:24:48] Speaker B: Right, whatever. All that means is there are idiosyncrasies to our product. I mean, just like yours, right, Same thing. But we didn't adjust properly in our process to account for those idiosyncrasies. The cloudy, non transparent nature of support issues is just one of the things we have to deal with. So how do we give engineers space so that they're able to work uninterrupted for multiple hours every single day so that we can actually make progress? Now, I'm curious on your end, big features that move things forward, how have those played a role in your growth overall? From the outside, it feels like when you release something big, it did change your trajectory. Like these, these few big steps over the last few years. [00:25:36] Speaker A: Yeah, I would say that there's, I mean, right now we're in the middle of a big feature called Roaster Pay, which is like our payment processing feature. And that's been, you know, that's one of those ones. This is where like the, the scar tissue kind of builds up around the product because it's like I said it'd be like, oh, we can do this in six months. We can have like a working version. We're now 12 plus months into it and it's like, we have, it's going really, really well and we're getting great response from our, from our users. But it's a little bit of like, we're understanding now the shape of the, of the iceberg and we're like, okay, so this is actually much bigger. Once you start to dip your toes into this thing, we're seeing that there's more that we could do. And what we're trying to do is take a step back and say, okay, we could do a thousand things in just the payment sphere and we could become a payments app if we wanted to. Right. Like that, that could be like the eventual. [00:26:26] Speaker B: Right, because you, you help wholesalers, you help coffee brands order from the Roastery. [00:26:33] Speaker A: Exactly. [00:26:34] Speaker B: So cafe, restaurant, It's B to B2B payment. [00:26:37] Speaker A: B2B payments. And there's, there's. So it's like, you know, could be that there's recurrent payments, there's Like a. You know, our. Our best case scenario is that the little coffee shop down the road is ordering through Roaster Tools, and then they're paying through our Roaster Pay Billing Corp, basically. But that's only one aspect of what we do. [00:26:54] Speaker B: Right. [00:26:54] Speaker A: So we also do production planning, and we also do. The whole sales part is kind of like its own thing. And so we've been looking for how do we evaluate our business and say, what is the priority? And so we've come up with, like, you know, listen to podcasts and there's like these, like the flywheel concept, which is like trying to basically say, like, what are the things that you do in your app every single day and where are the friction points and how do we reduce those? And we have things that are happening monthly. And it's like, you know what, though? That's too far. It's too long of a time for someone to be like, I got a lot of value there. So we're trying to say, what are the things that are happening daily and what are those things that kind of propel this circle of success around? Sounds great on paper, but it's still really hard to take all of that kind of insight and bring it down to the product level. So that's like. That's the process we're trying to do is, yeah, have the big view, cut it down, and then also prioritize correctly and actually estimate correctly segmentations correctly and. [00:27:52] Speaker B: Not overbuild and start with the most valuable things first. Yeah, it is a science. It's not math. It is real. It's real fuzzy. The problem we've had is we've had good growth. But you look up after a few months of focusing on the funnel and onboarding and activation and top of funnel ad creative and adding testimonials to the site to make it more credible. And then you look at the product and you say, ooh, we might be behind where the market is right now. And we implemented Churnbuster recently and we implemented Senya, and we also implemented Right Message. Right. So these three tools have provided an enormous amount of information over the last month. So Senya is testimonials. Great product. Super. I'm a big fan. It is awesome. That's almost like the positive aspect. So people who leave testimonials generally giving you, you know, good feedback. And inside of that is like, here's what I like about your product. Here's how it's changing my business. And that's like the most rewarding thing. You're like, oh, my God. This guy who rents paddle boards in a vacation spot literally can handle, right? You go on Google Maps, your business opens at 9:00am guess what happens at 9:01. You get 10 phone calls at the same time. Do you have anything available today? Because I'm on vacation. I'm going to rent the paddleboard. And homie was answering the phone himself. So he gets one phone call writing tickets, and the other nine are going to his competitors because he doesn't pick up the phone. And all of a sudden, Rosie picks up all 10 at the same time, and he's like, dude, change my business. He puts that on video, you share it with the team, and you're like, this is why we do it. Cool. [00:29:32] Speaker A: That's the upside. [00:29:33] Speaker B: The downside is Churnbuster. And when people cancel, they provide a reason for cancellation, and that is when you face reality. And a lot of those tickets recently have been around missing features, found an alternative. They can do this. You can't do it pretty straightforward. Like, if you develop these features, your business will be better. And then to start to really feel confident in what to build, and then to not be able to build it fast enough is when you start to realize, ooh, we. We need to make some changes. We got problems. This is. This is frustrating. So at least it's come with growth along the way. So I'm not freaking out and super angry. But. But it's. It's very frustrating. It's like, it's more like missed opportunity than, you know, no growth. [00:30:21] Speaker A: Do you have enough data to say, like, oh, yeah, it's like 75% of the people are saying one thing, or is it like you're looking out and there's like, just. It's spread out like a buckshot. [00:30:30] Speaker B: If I'm being honest. I have my own intuition. And then I look for evidence to confirm my bias. [00:30:39] Speaker A: That is. [00:30:39] Speaker B: And I think that's completely fine. I think a lot of founders should be fine with that. And I don't think you should always be driven by the data and ignore your feelings and emotions and gut. So that's the truth. In our company. There's a lot of confirmation, you know, seeking out confirmation of my bias, but I'm fine with that. And I like being right, which is fine. [00:31:04] Speaker A: I mean, obviously, it's been working well for you. Have you had any situations, though, where you. Someone's been like, hey, Jordan, this is too much, like, because I'm getting that right now from my wife, right? And I'm getting that perspective, and it's a nice balance from being the founder and having done my way. [00:31:20] Speaker B: I was going to say that you have the advantage and disadvantage of having a very honest business partner. So I think in my position, I don't hear nearly as unfiltered negative feedback as you do. I work with Rock and Jess, and we've worked together for 10 years, so I'm not like that worried that I'm not hearing any negative feedback. Right. Because we're pretty honest with each other at this point. The trust is there and the relationships are there. [00:31:45] Speaker A: Yeah. [00:31:45] Speaker B: But it's not as much. And there's. I feel it most when I am shown proof that alternative paths work better. Like, I love that Rosie is horizontal and has not chosen a vertical. You know what hurts? When one of our investors sends us a pitch from some verticalized AI solution and they've gone from like 1 to 9 million in ARR in like 18 months. And I'm like, hm, okay. [00:32:11] Speaker A: Okay. [00:32:12] Speaker B: You know. Noted. Noted. [00:32:14] Speaker A: Yeah. Yeah. [00:32:17] Speaker B: So there's. There's no shortage in points that prove you wrong, though, right? I mean, what. A lot of what we do is just ignore those. [00:32:24] Speaker A: What else can you do to go from zero to one on anything? You have to have that stubbornness to, like, just plow through, you know, like, sometimes you're like, nothing says I should be able to do this, but I'm gonna go ahead and create a business. I'm gonna do this thing. I'm gonna, you know, I'm gonna go and make it happen. [00:32:37] Speaker B: Yeah. Stick with it. Right. At least to some point. Right. You basically built. I don't even know what a CRM is that even under. Underdoing it. [00:32:45] Speaker A: Yeah. [00:32:45] Speaker B: You built a whole system on how to run a roastery. [00:32:48] Speaker A: It's like an erp, which is like the. Like, everybody cringes when you think about building an erp because it includes everything we've carved out accounting. Because that's like a. We don't want to go there. Yeah. Too much. That's too much. But. But it's like. I mean, it just shows how complicated our system is. And I'm like, yeah, too much. Too much for a small team. But it's okay. We're. We're making. We're making it happen. [00:33:09] Speaker B: Yeah. So coast. Obviously, you and I could talk like this forever, because we. We have been talking like this for. For 10 years. Our Slack Group is a. Is an interesting filter. We see what's going on out in the market, we see what other people are doing, we see what's going on, on Twitter. And then we kind of filter that back into our Slack group with, I don't know, a little skepticism. We're not hating. We like admire a lot of the good stuff that's going on there. We don't buy into a lot of the bullshit. And it's kind of very healthy in that way. But it's been pretty interesting seeing different approaches and different people's styles and all that in that Slack group result in different things, you know. So how does that affect you on like, you know, what do you want to do over the next year? Two years, five years? [00:33:56] Speaker A: I mean, I look at that group and we've all been at it for 10 years in some capacity in different forms. And there's like. And if you probably went back 10 years ago to where that formed, we actually physically met in person and we'd have this like kind of mastermind kind of like thing going on. And you probably could have painted where these pathways were going to go, like, personality wise. Yeah, yeah, yeah. So I think we're all getting older and I think there's something about that where we're like, okay, so now, mid-40s, what do we want to do with our lives? Is there some future career that we want to do? Is there something else? I think that's the question of are we satisfied? Because I think we're all in a position where we could continue doing this forever. This is successful. I think that's one of the interesting things. You look at that group and everybody's successful in their own way. Like, there's different flavors of that, of course, but it's like, yes, but undeniably. [00:34:48] Speaker B: Healthy, happy families, kids, businesses up and running. Like, yes, yes, absolutely. [00:34:52] Speaker A: Exactly. Yeah. So. And, you know, I think that there's always chatter of like, who's gonna bail and just be like, you know, just, just be like, I'm done, you know, and yes, yes. [00:35:03] Speaker B: I mean, we've. We've also had this interesting experience where one of the friends in the group had a spectacular exit. Just absolute home run. And what's he doing now? He's doing the same thing. He's working software, product management. I mean, yes, he sends us photos from, you know, skiing in the Alps. God bless. We demand those pictures. [00:35:23] Speaker A: Actually. [00:35:24] Speaker B: We're like, this is not okay. You need to send us some, some pictures from the lifestyle. But he really likes what he's doing. [00:35:30] Speaker A: Yeah. [00:35:30] Speaker B: And for me, I know at least that helps me see that as like a. That might be a financial milestone, but it doesn't. It's not the end. And you still have thinking to do and you still have decisions to make on what you want to do during the day, what you want to do with your life, what you want to focus on. [00:35:45] Speaker A: Yeah. Yeah. [00:35:46] Speaker B: I've been thinking about this a lot with my brother selling his business. I think about that with another friend in the group considering selling. Yeah, it does feel like mid-40s, kind of like, should I keep going down this path or do I want to change it up? [00:36:01] Speaker A: I don't know about you, but, like, physically, I like, you know, getting up out of bed in the morning and, like, if. If I don't do a workout, like, you know, if I'm not working out, I feel it. And so I do feel like there's a little bit of, like, the clock's ticking. My kids are getting older. [00:36:14] Speaker B: Energy wise. [00:36:15] Speaker A: Energy wise. Just like. Like, the things I could do, like, 10 years ago and not even feel it are now I have to, like, think about it a little bit more and, like, you know, I'm getting a little bit older. I don't know, maybe that's just me. Maybe I'm. I'm a. I see. I see the skepticism on your face here. [00:36:31] Speaker B: I'm just. I'm just thinking of. Of how well I performed at paddle last week on Sunday, and how I beat the number one team, so. No, I hear you. I think what you're describing is, like, maybe 10 years ago, staring at the computer, trying to make money come out of it, to improve your life and your family and all this other. [00:36:51] Speaker A: Like. [00:36:51] Speaker B: Like, that was kind of enough because there was. I don't know what else was going on outside of it, but I didn't mind sitting in front of a computer the same way that I'm more thoughtful about it now and thinking, hmm, is this what the. The way I have described it to myself and to others over the last few months is? It does seem appealing to move up another layer of abstraction in the business stack. Less operating, more managing and investing. And it is a bit odd to say, but my employees have gotten used to my management style being pretty close to that. I don't execute that much, but everyone's kind of okay with it because everything's kind of going in the right direction. So today when I wake up and I'm in absolutely no rush to get to work, I'm taking my time, and I'm going to the bakery, I'm buying a challah, calling my mom. You know, I'm, like, taking my time on Friday, but along the Way I had an idea that we should take the Rosie phone number and put it at the beginning of the onboarding. Now that our model and our scraper is so good, because more than 50% of the people that make a test phone call put their cards on file, but we have it at the end of our onboarding. And so my, you know, my idea was, what if we put it all the way right when you. The first screen you see is the phone number and then it says, okay, make a call and then go into the customization and it's that kind of random thing on a Friday that changes the percentage of people that convert. [00:38:20] Speaker A: Yeah. [00:38:21] Speaker B: And everyone's kind of gotten used to, well, Jordan's kind of useless and then all of a sudden, very useful. So I don't know what that means for, like, the future, but I don't know if it's going to lend itself to remaining that way or to being even better as the company grows or if that's really good for the next business. I really don't know. [00:38:40] Speaker A: It's obviously a skill, though. Like, it's something that, like, if you get better at that, you multiplied everything you do versus, like, being the individual contributor that just kind of types away. Yeah. So, yep. I, Yeah, I think that, you know, for me, my goal at this point is I want to build a successful, sustainable business that values my personal time as much as my, like, business time. And realizing that I've always been on this trajectory that's not going to have the hockey stick, like, amazing thing, but we built a great business and that's good enough at this point. So there's actually a little bit of acceptance at this point for, for where I am and what I'm doing. And could there be a great exit at the point, you know, not now, but maybe in a couple years, you know, this, we're heading there. So. [00:39:28] Speaker B: Right. If it, if it stays on the trajectory, it reminds me of a business, of someone that I coach in the tiny seed, like SAS Institute thing, similar thing, desktop software, very long development cycles because you only release something when it's perfect, but been doing it for 15 years and it is a beautiful business. There is zero to complain about. The growth rate does not matter. It's not that it doesn't matter at all, but in comparison to how healthy of a sustainable business and what it provides for this founder's life, it is fantastic. Yeah, I think that's a great place for us to end. [00:40:04] Speaker A: I love it. [00:40:05] Speaker B: John, it's great to see you, man. I hope that we can come visit Mexico or you can come up to the Midwest sometime soon. Both. [00:40:11] Speaker A: Let's. Let's make it happen. So thanks for joining, Joy. Appreciate it.

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