October 29, 2025

01:02:14

Envy Fuel

Envy Fuel
Offsite
Envy Fuel

Oct 29 2025 | 01:02:14

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Show Notes

Could sharing your most shameful moment actually accelerate your career? 
 
Jordan Gal teams up with fellow entrepreneurs to discuss work and life beyond business. In this episode, Jordan sits down with returning guest Christian Genco,a software engineer and entrepreneur navigating the challenges of scaling products while maintaining focus. Christian recently welcomed his second child and shares insights on balancing creative work with reactive demands. What's the real cost of constant interruptions on engineering productivity? The conversation explores vulnerability as a business asset, the concept of "Sanskara" (emotional wounds from Sanskrit that block growth), and practical strategies from 37signals' Shape Up methodology. Christian opens up about getting fired from a startup and how sharing that vulnerability created unexpected opportunities. Can founders really separate engineering focus from customer chaos? 
 

In This Episode:  
 

  • (00:00) How Sharing Shame Creates Unexpected Business Opportunities 
  • (05:48) Christian Announces His Second Child 
  • (13:52) The Creative Satisfaction Problem in Business 
  • (24:52) Managing Reactive Engineering vs Deep Creative Work 
  • (42:19) Founder Intentions and Life Philosophy Beyond Money 
  • (56:22) The Engineering Productivity Challenge Every Startup Faces 
  • (59:37) 37signals' Approach to Protecting Engineering Focus 
  • Share with someone who would benefit, like and subscribe to hear all of our future episodes! 

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: 
Christian Genco X: https://x.com/cgenco   
37signals (company) - basecamp.com
Rosie AI: https://heyrosie.com/ 

Chapters

  • (00:00:00) - Off-Site Podcast
  • (00:01:52) - Why I Talk About My Mistakes on My Podcast
  • (00:05:48) - Baby Luca's First Birthday
  • (00:08:39) - What Do You Need To Know For A 3-Year-Old
  • (00:10:54) - Has Having a Baby Impact Your Worklife?
  • (00:14:40) - Sponsoring an AI startup
  • (00:15:05) - How to Focus On Work and Family
  • (00:16:50) - "You Ruined My Wedding!"
  • (00:18:46) - How to Stop Reacting to Customer Support Emails
  • (00:23:51) - Patrick Collison on His Personal
  • (00:28:28) - The Secret to A Nice House
  • (00:31:10) - How to Let Go Of Envy
  • (00:34:47) - "I Can't Control My Own Life"
  • (00:38:12) - The Lean Startup on Postmortem
  • (00:42:42) - A Boss Had a Fight With His Employee Over Communication
  • (00:47:32) - How To Deal With Conflict In Your Relationship
  • (00:51:03) - How to Manage Expectations in the Software Development Process
  • (00:56:30) - How to Manage a Non-Technical Team
  • (00:59:37) - Software Development: The Hill Chart
View Full Transcript

Episode Transcript

[00:00:00] Speaker A: There's this term sapskara that comes from, I want to say, Hinduism, that this idea of a sapskara is this emotional wound that that like gets tangled up that you're not able to release. So like back in high school when I got sent this email that created, in this terminology, in this phrasing that created a subskara that then like there's this emotional blockage that then anytime something similar hits that, it's the same sort of feeling. And it, he describes it as like this circle that's going around and kind of feeding it on itself. And so that's releasing those subscribers, I think is the ultimate game. [00:00:29] Speaker B: Welcome to the off site 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, everybody. Welcome back. Another episode of the off site podcast with my friend, Christian Jenko. [00:00:55] Speaker A: Oh my gosh, you got, you got my name right. [00:00:59] Speaker B: I worked on it. [00:01:01] Speaker A: I believe you. Yep. [00:01:03] Speaker B: So, Christian, we just had the podcast before the podcast. [00:01:07] Speaker A: We did, yeah. A long, long conversation, but it was good. [00:01:10] Speaker B: Now we're, we're switching from fully private to semi private. It's just us, but maybe other people listen to. [00:01:17] Speaker A: Yes, I would love to if we could move more of the private stuff into more of the semi private stuff because it was a very interesting conversation. There's a lot going on. [00:01:26] Speaker B: Yes, it's tough because the, the more honest and vulnerable, the better. But there is a line on some things actually shouldn't be made public. And it's tough to know where that line is. It's usually a bit past where the comfort actually is. That's where the good stuff is. But here we are. We'll see what we touch on around those topics as we go. [00:01:52] Speaker A: So a point that I made earlier was like, I have found tremendous, like, it's, it's so vulnerable to talk about things that you're ashamed of and like the. On my podcast, after I got fired from the startup I was working on, like, that's a vulnerable thing to talk about. And my goodness, the warmth and love and support that I got from other people of talking about, oh my gosh, I was in the same sort of position and I was able to turn it around and people like being like, oh, you seem like a good guy. And there's this opening of my company, like, do you want to, do you want to interview for them. Like, oh, my gosh, it was. It was wonderful that the. I feel like the more I've been able to walk in that direction, that the more support I've gotten and the more I felt like it's not just me going through this stuff. Yeah. [00:02:28] Speaker B: It's stronger connection when you're honest and vulnerable because everyone has it. And then when it gets let out is when the, like, the relationship builds over time and just getting to know what someone's doing, how they do it, their personality, and then when you kind of reveal, you open the door a little bit to vulnerability. That's when, like, the. You really feel the connection. And I think. I think all of us get that. And you know, what comes to mind is a funny thing. I kind of can't stand Jason Calacanis at this point. Oh, I'm a little. I don't know, it's just. I get sick of him. [00:03:00] Speaker A: Okay. Now I don't think I know who that is. Who's Jason Calcanis? [00:03:03] Speaker B: Oh, jcal is one of the guys from the. The foursome of the all in podcast. [00:03:08] Speaker A: Okay. [00:03:08] Speaker B: He's been in, like, startup media for a very long time. [00:03:11] Speaker A: Okay. I recognize the name. Yeah. Okay. [00:03:13] Speaker B: And he told a story once on a random podcast. It was like in front of a classroom of. Of entrepreneurship students or something. And he told us the story of when he sold his first company and when he was in his crappy little Manhattan apartment with his wife or fiance at the time, and how he was refreshing his bank account when it hit and how he cried when it hit. And like, you know, and it. That conversation was so vulnerable and real, and I connected with it. So I still, no matter what I dislike about him, I have that thing, that connection and that, you know, identifying with those emotions in such a powerful way that he kind of always holds. There's always something positive in the mix of what I think about this person. And I think that that happens, you know, that happens with politicians. It happens with media people. It happens a lot. I think podcasting is particularly good at it because the voice. [00:04:13] Speaker A: Yeah. [00:04:13] Speaker B: You can't really lie. [00:04:15] Speaker A: Yeah. Yeah. [00:04:15] Speaker B: You can't hide the same way. [00:04:18] Speaker A: Yeah. Especially in long form. If it's like an hour long conversation. Yeah. [00:04:20] Speaker B: Yes. You kind of honestly get to know the people much deeper than. Than in other scenarios. And this makes me think of speaking of something. More recently, Ian and Aaron did a podcast talking about Aaron's like, vision quest. And his vision quest was basically, you know, he went out, out of town for a few days and thought about his work from a different perspective and his productivity and what was holding him back. And he shared that vulnerability around feeling a little crappy about being on the phone too much and being addicted to Twitter, like a lot of us. And the reaction that he got from that, I think, speaks to the same type of thing. Right. People admire you. That's one level of connection. They like you. They find you funny. It's one level of connection. And then the vulnerability, weakness, exposure, shame, all that, that, I think is just much more powerful. [00:05:18] Speaker A: Yeah, yeah, yeah. That's. That's what it means to be human. I think I'm reminded of, like, Brene Brown's gifts of imperfection, this idea that if you've been through hard stuff and if you. If you struggle with hard stuff and like that, that give you a strength then to be able to help other people through that same sort of thing. And the more that you're able to talk about that, the more that you've been able to, like, if you have a podcast, then about, like, oh, my gosh, I got fired from this job, and it felt terrible. Okay, well, now. Now you can attract all these people who are in the same sort of position but feel that same sort of shame. Don't want to share that. And, yeah, it just. It makes the world better. I think that's an important part of humanity. [00:05:48] Speaker B: Cool. Speaking of making the world better in humanity, you have some good news, my friend. [00:05:53] Speaker A: I do, yeah, sure. I. Sarah and I have done our part to improve the plummeting birth rate in the Western world. One more time, we have a small update of a small little baby. [00:06:06] Speaker B: Small update, small child. [00:06:07] Speaker A: Luca Jenko. Small update. Luke. [00:06:10] Speaker B: Beautiful. When? Last few weeks. [00:06:12] Speaker A: Yes, like, end of September. Really close to Isabel's birthday also. So they're. They're almost exactly two years apart. Went really smooth. There was. There was some stuff around the. That we had to do a C section both times. C section wasn't the. Wasn't the plan. But, yeah, it worked out well, and we knew a lot more about what to expect this time. Just all around the. The analogy that I've been drawing is if you've ever. If you've ever learned how to ski, especially as an adult, like, you remember what it feels like to learn how to ski. It's brutal. You. I. I learned when I was young, but, like, I've. I've. I've taught a few people how to ski as adults, and, like, you're just falling down and bruised and you're exhausted and you're on the bunny slopes and you're not going very fast and it's not fun and it's just this sludge for days of, of going through that and then you look and you see like this 89 year old dude just zipping down the black diamonds because he's been skiing forever. And, and it feels effortless and in flow and beautiful. And so it feels like between Isabella, our first child, and Luca, our second child, it feels like we've moved more in that direction of competency of that 89 year old dude where we know what corners to cut. Oh, there's a great example I have, of course. [00:07:10] Speaker B: Important versus not important. [00:07:11] Speaker A: Yeah. The whole game of parenting, I feel like, is figuring out what you don't actually need to be doing. So when, when we first got to with Isabella, we, we did things like the most complicated way we possibly could. So we were trying to do breastfeeding and pumping and formula because we didn't quite know what was going to work. And on just one tiny example of that on the formula, if you look at the instructions of how you're supposed to do it, it tells you to boil water and then wait for the water to cool off to whatever 170 degrees and then mix in the formula and then don't shake it. You stir it around to not introduce bubbles and then you can feed it to the baby. Okay. So I tried to do that like, like half a dozen times. I did the whole. And you got to cry and screaming baby. And you can't pre boil the water. You got to like fresh according to the directions. And so I'm looking at this like, oh my God, this is. And the baby's crying the whole time. It's like this 20 minute process and I've got this boiling water in one hand of the baby. It was, it was a mess. And then I saw this YouTube video of this woman in like Queens or something and she was like, ah, I just use tap water. [00:08:02] Speaker B: Yes. [00:08:02] Speaker A: She just took a scoop and put it in and shook it. And I was like, oh my God, you can do that. And I tried it and it was fine. Yeah, she loved, she was much happier and the room temperature water was fine. And yeah, so, so, you know, there's, there's probably a thousand things like that that we realized you don't really need. Right. [00:08:16] Speaker B: I remember we like pureed our own baby food for the first. It just progressively gets a more relaxed approach to the baby is just going to be fine. And it's not like, oh, cut every corner it's. Just relax a bit. Just relax. Focus on what's actually important versus not. [00:08:33] Speaker A: Yes. And babies are much more robust than I thought they were. [00:08:36] Speaker B: Yes. And the stress actually doesn't help, but that's great. So you have two now. [00:08:40] Speaker A: You have two. Yeah. [00:08:41] Speaker B: Okay. [00:08:41] Speaker A: Okay, cool. [00:08:42] Speaker B: We have three. I remember baby time was. It's. It is fun and exhausting and what everyone says it is, but I really enjoyed that, that transition from one to two on just, I guess maybe being able to enjoy it more and stressing less. [00:09:00] Speaker A: Yeah. [00:09:00] Speaker B: I remember laughing after we had our second, and we would be like, well, we're going to go meet someone at the park. And then we would just kind of grab our stuff and leave. And we would compare that to the first one. It would be like this 30 minute ordeal to get out of the house. [00:09:16] Speaker A: Yes. [00:09:17] Speaker B: And then. And then, you know, we had. We had a third. Not sure if you're planning on a third. Do whatever you want. But then the third was, you know, even more extreme. And it gives you this confidence as parents that, oh, okay, you know, we're fine. Yeah, we're. Are we the greatest parents in the world and know absolutely everything? No, but it's fine. The kids are great and we love them and they love us and we're doing all the right things and great. [00:09:37] Speaker A: It's funny, you have the example of going to the park. That's a. I remember distinctly the moment when I decided to go out with Isabella to a park or to the museum, I think it was. And we just left. We, like, she had a dry diaper on and she, you know, we were in the middle of toilet training, so I was like, oh, you know, we'll try to go while we're there. But we didn't bring any snacks. We didn't bring any bags. I didn't bring a change of clothes. I just put her in a car seat and we just left. And oh, my gosh, you're. You're a human. Like, this is great. And even now with. With Luca, like, I feel like I have a much more in tune sense of what we'll actually need. So Sarah. Sarah likes to be prepared. And, you know, if we're all going somewhere as a family, she'll, like, bring a whole bag of stuff. And I have no idea what's in the bag, but it's a. It's a much smaller bag than it used to be. [00:10:17] Speaker B: But, like, it's a bag to make the parent comfortable. [00:10:20] Speaker A: Yes. She. It's an emotional support bag. But, like, when I'M going somewhere with Luca and Isabella. I need a spare diaper for Luca and a little, like, a Ziploc bag of wipes and milk. So we'll bring, like, depending on how long we're going for. But Luke is breastfeeding, and he's breastfeeding really well, so sometimes we don't even need that. And I just feel like, oh, we got. We got everything. It's just in my pocket is everything we need. Right. [00:10:43] Speaker B: Then you get into the fruit smoothie packs. [00:10:46] Speaker A: Oh, yeah, yeah. I'll put a yogurt pack in my. Right. Then you're good. [00:10:49] Speaker B: You literally do anything. [00:10:50] Speaker A: We're good for like, eight hours. Yeah, yeah, yeah. Yes. [00:10:54] Speaker B: So how have. Has it impacted your. Your working life? [00:10:59] Speaker A: Do you juggle more? Yeah. [00:11:00] Speaker B: Or are you. Are you more pressed for time? Do you feel more stressed? Do you feel more ambitious? Like, you know what. What has it done? [00:11:06] Speaker A: Yeah, yeah. You asked me a similar question about Isabella. And so certainly he's. He's a month. A month and a week old now, which is what, five weeks plus two days, I think. And so, like, yeah, first month. I just wrote myself a blank check of, like, nothing needs to happen. Just what you're. We're adapting. Like, cool. You want to work on a fun project. So I, like, upgraded our network and bought a new router and upgrade. We have a home security system. [00:11:30] Speaker B: Okay. So you took the pressure off yourself. [00:11:32] Speaker A: Yeah. So last time we talked, I had this whole plan of, like, oh, I'm going to, like, do this email marketing plan. And, you know, I have this two week sprint left on file inbox to like, get it to a. And none of that has happened, and that's fine. So that's. And we're. We're gearing back into it now surprisingly quickly. I remember with Isabella, it took me particularly with sleep deprivation. It took me like, maybe seven months before I felt like I had my first day of like, okay, this feels. This feels like a 60% day of what I might have had before. And I've already had several of those. Everybody's sleeping, everybody's happy, everybody's pooping and eating. And. Yeah, so it's. It feels just much easier all around this time. [00:12:06] Speaker B: Just reverting back to normal. Just smooth the path. [00:12:09] Speaker A: Yeah, yeah, yeah. I had a full workday on filing buck yesterday and, like, got a bunch of this stuff done, and he. He came two weeks early. And so I was planning on like, all right, here, here's the two week sprint. Let's go and get this done. And Then I can take a break. And the state of limbo. [00:12:21] Speaker B: Yeah. [00:12:22] Speaker A: I have these customers emailing me like, when's this thing going to be done? You told me it was going to be like, whatever. And I was like, sorry, I got a baby. This happened instead. Yeah. [00:12:29] Speaker B: What a privilege to be able to take that time with Fan. [00:12:32] Speaker A: I know. [00:12:33] Speaker B: I always like, look over to, you know, other people's more, more corporate work and going back to work, you know, within a week or two for the dad. And then you know what always feels incredibly fast for the mom to go back to work after, you know, two, three, four months. [00:12:49] Speaker A: Yeah. [00:12:50] Speaker B: It's one of these things where I don't often feel European and I very often think they do things the wrong way. And I can acknowledge that 12 months of maternity leave would be. I can understand from an employer point of view how that's a bit absurd, but when you look at a young mom and a young baby, that's when you really are like, we should figure something out that's better than three, four months. [00:13:13] Speaker A: Yeah, yeah. It's a tricky balance between, you know, the individual and the, and the economy of how you do it. Sarah actually works for a Spanish company, so we get to enjoy living in the US and having more of a European style maternity leave. Interesting. [00:13:27] Speaker B: There are companies in Spain that hire Americans. [00:13:30] Speaker A: There are, yeah. Because they're expanding the U.S. it's a, it's a buyer side company. Qbeam Q U I B I M. They, they do AI processing on medical images and so of course they want to be expanding more of the US market. Right. So Sarah, I was higher number two or three in the US and she's fluent in Spanish. She, she spent a year or two studying abroad in Spain. So it was, it was great hire for them. She has a bio biomedical background also. So it was. Yeah, it was really good. [00:13:56] Speaker B: Very cool. Yeah, yeah, that's one of those fields. We don't have HIPAA compliance, but we get a lot of demand so I think we'll do it soon. Hippo compliance also has turned into this like very easy thing to do. [00:14:08] Speaker A: Yeah. [00:14:08] Speaker B: Company called, what was the, the big one. I'm blanking on the name, but there was one that did like SoC2 and all the GDPR and HIPAA, all that. And it did really well. And then a few companies came out and started using AI to get that stuff done faster and now it has turned into ridiculously easy. It's like, here's 5,000 bucks and one week and you're, you're Compliant. [00:14:33] Speaker A: Oh, wonderful. Okay. I know a lot about HIPAA. I was just gonna roll that myself, but SoC2 still felt kind of scary. I think the last quote I got for that was like, 20 grand to do it. So. Yeah, that's. If that's gone down with AI, that's. [00:14:43] Speaker B: Has gone down from what it used to be. I remember at rally, we thought about a lot of it because we had the payment fault and we want to go into Europe, all that, and it was like. It was a real barrier. It was, like, super painful now. Yeah. The company we're looking at is called Delve D E Del V E. Yep. They do a really good job at making it extremely efficient. If they're interested in sponsoring, call me. [00:15:05] Speaker A: All right. [00:15:06] Speaker B: What do you got going on this week? I had a mixed week. Very stressful, very difficult, and good on the growth side at the same time. [00:15:15] Speaker A: Yeah, I think. I think my primary focus now is kind of finding the new balance of the family and with work. And I got a few days done on. On file inbox of pushing stuff forward with that. The biggest, like, the. The vulnerable conversation I could be having around file inbox is this emotional block I feel like I have with customer support emails that for whatever reason, it just. It creates this, like, tumultuous. It's like this anxious heat. Just opening up the inbox and reading the messages, and then that kind of feeds in on itself of I don't want to do them. And then I'm waiting more time to do it. And then I feel shame about it because I'm like, oh, my God. I haven't replied to this person in a month. Like, what am I? What kind of a piece of shit am I? That I'm that? And so something that's been really helpful for that recently is I've been having these kind of, like, coaching calls with a friend of mine. I don't know if you know Dave Setia. He. He has an app called Recut. It's an eight event. One of my. One of my best friends. We've had weekly calls for, like, the last two years, I think, but I will get on the phone with him. We've done this, like, the last two weeks now. And I just open up the inbox and I share my screen and I talk with him about what I'm feeling, and I'm like, okay. I feel this heat in my stomach reading this message, and it's. Oh, it's like coming up to my shoulders and kind of going around. And he recommended this book called the Importance of Focusing, I think, is the name of the book that has this whole method of, like, okay, here's how you can kind of personify these feelings that you're feeling and talk to them. And that's. It's been wild because, like, the conversations we're having, I'm like, okay, now, now the egg in my stomach has, like, cracked through its shell, and the heat's going up here, and I'm like, I'm listening to myself, like, what the hell am I talking about? But it's been really helpful. [00:16:44] Speaker B: Okay. I like this stuff because I think all. All of us experience these things. [00:16:49] Speaker A: My. [00:16:50] Speaker B: My first question to you is, is it proportional, the support ticket that you get? You know, sometimes it's like, you have wrecked my business for the week because I can't accept X, Y, and Z from my customers. [00:17:01] Speaker A: And. [00:17:02] Speaker B: And, you know, I regret ever using your product. Like, sometimes it's really heavy. Yeah. And it's understandable to just, you know, have that wreck your day. Like. Yes. Sometimes it's so disproportional. [00:17:14] Speaker A: Yeah. [00:17:14] Speaker B: Someone's like, how do I do X in your product? And you're like, screw this person. Why did I get into this business? I hate soft, you know, so. [00:17:22] Speaker A: Yeah. Yeah. [00:17:23] Speaker B: Do the reactions, your reactions feel appropriate? [00:17:26] Speaker A: Absolutely not. No, no, no, no. It has. It has almost nothing to do. And there's, you know, if I were in a different frame of mind, I could find a way to justify that they were proportional. Like, I'm remembering an email that I got where someone had this phrase, you ruined my wedding. And that was like, oh, yeah, yeah. But also, like, reading the email that had nothing to do with me. The thing. The specific thing she was complaining about was that the QR code that she printed didn't work. And I don't make QR codes. And so what? I don't know exactly what happened, but. [00:17:50] Speaker B: I think someone expressing their emotions to you, they're trying to transfer it to you in some way. [00:17:56] Speaker A: Right. And then you can also, like, what are you talking about? I'm a service that we're going to use to, like, collect your photos and that ruined your wedding, that they weren't able to send you the photos right away. What are you talking about? [00:18:05] Speaker B: Right. You're being disproportional. So I'm not going to react in that way. [00:18:08] Speaker A: Right, Right. That it had nothing to do with me. And, like, even in cases where it feels like I could justify that it did have a lot to do with me if it. If, like, my service went down and someone was like, hey, I lost a day of business because this thing went down or something. Even then, I think in my current, the current way that I'm framing it, that still has nothing to do with me. I do feel a responsibility of, like, I want to be doing it, providing a good service, and I'd like to be fixing that. But at the end of the day, you know, emotionally, there's not very much different between that and the woman who's saying that I ruined her wedding because the QR code didn't work. So that's kind of where I'm pulling myself back to. Of like, this is. This is entirely an internal game. This is entirely just better understanding myself and my emotions. Like, what is. What is the seed that this came from? So something Dave asked me that was really useful was like, what does this remind you of? Or like, what's the first time that you remember feeling like this and pulled back all these stories of like, in high school. Yeah, yeah, yeah. I. In high school, I was part of the theater department and I was getting good at websites and I had just redesigned the website for the. For the whole high school, and the theater department had their own separate website that was kind of shitty. And I was like, oh, let me, like, do a nice thing for them. I'm going to go and redo their website without them asking. I'm just going to, like, redo it as a gift and then give it to them. And so I did, and I emailed the theater director, and a couple days later, I get this email back that was like several cc's and like, back and forth between the theater director and the. The parent volunteer who had made the website, who apparently had some pride in that, like, she was good at making websites or something. That was back and forth. And the way that I had phrased it was like, hey, your website sucks. Do this great favor by making a better one, okay? And like, I remember reading that email as a, as a high schooler, I might have been like 12 or something. And it was that same sort of feeling that I'm. That I'm getting from these customer support emails of like, this shrinking and like this. He, like this our shame of that. Oh, I do something right? But I got punished for it and I actually hurt someone by doing it. And that feels bad and confusing. And it, like, I still can't quite wrap my head around how are those things connected and like, what's the core of those things. But this feels like the right sort of problem process of like, at an Emotional level, indexing memories by feelings and like, really paying attention to the physical sensations of what this is. I feel like I'm finally, and this has been a problem for me for over a decade now of like, feeling these sorts of negative feelings around customer support emails. But it feels like this is what's unearthing it and solving it at a. At a base level. [00:20:18] Speaker B: Interesting. So for a solution, do you go toward a better understanding of yourself so you can manage those emotions better, or do you acknowledge that this type of interaction triggers you and pushes you in the wrong direction, that you should create distance from it? From my end of things, I have created distance between myself and support emails because like you, I end up in a spiral of. I don't really want to answer this right now. Yeah, I'll answer tomorrow morning. [00:20:50] Speaker A: Yeah, yeah. [00:20:51] Speaker B: And then the day goes by and then it's three days and then you don't even know. Then I'm going to email them and explain to them why I haven't gotten back to them. And so it's a spiral for me. [00:20:59] Speaker A: Yeah. [00:21:00] Speaker B: And so I have created distance. I remember at Cardhook when there couldn't be distance. Cause it was, you know, just me and then technical people. So clearly it was my responsibility. And Carthook was real close to the. To the money, real close to the fire. Right. Someone's checkout. So we had multiple support issues around. You cost us $40,000 today, you know, like. And they were right. So I had to create distance because I couldn't function as CEO and think about what needed to happen next. And when I was enmeshed in the customer support emotions, now we have someone full time and she's incredible. And the investment required is so there's. So there's so much leverage. And it's not like we're underpaying her. Like, she's so happy. And we recently came to her and we're like, if you want to do support on weekends, we'll pay you time and a half. And she was like, absolutely. And she's so happy. And we're so happy. So I guess what I'm saying is there's a range of possible solutions. Do you want to get better at it and manage emotions better, or do you want to create distance and kind of knowledge? [00:22:16] Speaker A: Distance. Distance is the most pragmatic solution, especially optimizing for a functional business. And I've done that. I hired an executive assistant to do that. And I have this whole project of like automating it with AI and that sort of Thing the way that I'm currently framing it is. And this is not as good at a business level, but this is an opportunity for me to personally grow, like, to be confronted with these bad feelings consistently. There is no other area in my life where I can, like, consistently kind of surface these negative emotions. And so that, for me is pointing to. There is something here deep down that, like, is an opportunity for me to reach, you know, closer to spiritual enlightenment. And so I'm. I'm very intentionally kind of viewing it in that way of, like, this is my emotional exercise week of, like, let me. Let me go through and just kind of face these feelings and do it. That's not as good for the business. Like, for the business. That means that people are getting an extra few days before, you know, if I hired someone, certainly that'd be getting replied to faster. But, yeah, that's. That's where I'm at right now. Kind of looking at this more as a long term. You know, the true game that I'm playing is not that I'm trying to grow file inbox to the moon. This is a game of, like, how do I. How do I better understand myself? Yeah. [00:23:24] Speaker B: Okay, Interesting. I know whenever I read comments around founders doing customer support and how important it is, and you know, you see the Carlson brothers still doing support on Twitter, things like that, I can acknowledge that it is. It can be better to be that in touch with your customers. And I can also say, well, me personally and through my experience, I'm not one of those founders. [00:23:49] Speaker A: Yeah. [00:23:49] Speaker B: And that's okay. [00:23:50] Speaker A: Yep. With the constants too. I wonder, because I've gotten like, personal emails from Patrick before, and I'm like, oh, my God. After, like, you know, it was 30 minutes, I think it even replied with something that exactly helped me with my problems. I. Something I wonder is, like, are they at a point where they. Where they feel like, are they not merely emotionally more grounded in the business? Because something that I'm uncovering and doing these exercises with Dave is like, a lot of these feelings have to do with that. I know that file inbox is not the product that I want it to be. And so people will say something like, hey, I tried to do this thing and it didn't work. And then I'll be like, oh, my God. That's the thing that I've been wanting to do that I feel disappointed myself that it's not there. And so kind of what I'm. What's part of what's. I'm really excited about in going through these sort of deeper exercises is I can see how it would feel very different if I can align myself emotionally. Nothing necessarily has to change in the business, but just kind of like, addressing those feelings of. Of shame and kind of like feeling like my identity is tied up in the business and. And that if someone's criticizing. You know, when I read the. When I read the email that says, you ruined my wedding. Well, what she's saying is, you know, something about your product wasn't working. But I really feel that deeply of, like, oh. Like, I personally, it feels as if I walked in and, like, knocked over her wedding cake or something, like. And so. So if I can get to a point, I think, where I feel more of that disconnection of, okay, this is the business and I feel proud of it. And, yes, it's not perfect, but it'll never be perfect. And I know that it's helping a lot of people. Is that not emotionally where someone like Patrick Collison is? Where. Because, my God, he runs. It's like 20% of all commerce on the Internet or something runs through. Runs through stripe. Like. Yeah, I'd feel great about that. Yeah. [00:25:24] Speaker B: I think growth, success, comfort, money, they all can contribute to a healthier response. You know, more grounded, but just more confidence. You know, when someone gave bad feedback on Rosie's, I don't know, agent quality or how she handled something on the phone in month two or three, I was you filled with shame, just embarrassment. And it's almost like a position of weakness, you know, apologetic. [00:25:52] Speaker A: Yeah. Yeah. [00:25:53] Speaker B: And now, you know, 1200 customers or whatever it is, you're like, yeah, it's not perfect, but Churn isn't crazy. So it's not like everyone's miserable. It's just, you have more customers, you have more support. Okay, so let's do a good job at replying and adjusting. But it doesn't have. It doesn't pierce nearly as deeply. [00:26:11] Speaker A: That's where I'd like to get to. I'd like to get to the place where it doesn't pierce as deeply. And I've been telling myself a story of that Things need to change in the product and in the business for me to not feel that way. And I'm. I no longer think that. I think this is an internal game. I think this is. I think getting through this is going to look a lot like unraveling. I've gotten really into spirituality. Yeah. [00:26:30] Speaker B: Peeling back some layers. [00:26:31] Speaker A: Yeah. Yeah. There's this term, Sapskara, that comes from, I want to say Hinduism. That I'm listening to a lot of, like, Western people who pulled stuff over from Eastern traditions, and the idea, like Michael Singer has been a big one for me. And this idea of a Sapskara is this emotional wound that gets tangled up that you're not able to release. So, like, back in high school when I got sent this email that created, in this terminology, in this phrasing that created a Sapskara that then, like, there's this emotional blockage that then anytime something similar hits that, it's the same sort of feeling. And it, he, he describes it as like this circle that's going around and kind of feeding it on itself. And so that's releasing those subscaros, I think, is the, is the ultimate game. [00:27:07] Speaker B: Whoa. Well, I, I, I have to acknowledge, as you describe that that hit so close to home that I almost tried to, like, block it because I, I could, you know, I can. As you were saying, that I, I'm like, ding, ding, ding, ding. You know, I can like, identify a few of those. [00:27:23] Speaker A: Yeah, yeah. And those are scars. That was, that's what it was like. [00:27:26] Speaker B: Yes, absolutely. I have described it before as the dragon I carry around that I want to slay. But, but it. Maybe that's like a way to visualize it or personify it or something, but it might be more accurate internally to, to describe it the way you did. I will tell you, when I, When I walk into a nice house, for me, that's the, that's the most emotional, most emotionally poignant or powerful version of that scar. For me, when we, when we first came to this country, we had no money. My family's kibbutz. Nick, when you live on a kibbutz, you literally don't have your own money. [00:28:04] Speaker A: People don't. [00:28:04] Speaker B: Didn't have their own bank accounts. [00:28:06] Speaker A: Sure, sure. [00:28:06] Speaker B: You just have what's called tax eve, which is like your account. So you go to the store and just, like, grab your stuff and, you know, put on my account. So you literally don't even use money? [00:28:16] Speaker A: Yeah. In, In a kibbutz. Is the store. Is that like a communal commune? Communal thing or it's. [00:28:20] Speaker B: Yeah, it's in the community. [00:28:21] Speaker A: You're not going to a Walmart. [00:28:22] Speaker B: Like, you're, no, there's like a little, Little store. I mean, you leave sometimes and go to other stores, but, you know, but I was a kid, so I didn't know. All I knew was like, money doesn't matter because you're in a commune. So when we first moved here, we didn't have a Very nice house. We were just trying to get our feet under us. [00:28:36] Speaker A: Right. [00:28:36] Speaker B: I'm like. It's what. I came when I was 6, so these experiences that I'm like 8, 10 years old, and I. My house is not that nice. And I would walk into someone's nice house, and it would just, like, so powerful. I mean, it's still what I carry around today. And why? Nothing. I like nothing more than beautiful houses in real estate. [00:28:58] Speaker A: Interesting. Yep. [00:28:59] Speaker B: And that's the most powerful version. And it's not. [00:29:02] Speaker A: Yes. [00:29:03] Speaker B: It's a physical, like, oh, beautiful house. Cool. But really, it's. It's to switch positions. Yeah. And be the family that lives in the nice house. And when someone walks in and is like, what a beautiful house you have, I cannot describe to you the level of satisfaction that gives me now at this age. [00:29:22] Speaker A: Yeah. Yeah. Fascinating. [00:29:24] Speaker B: Yeah, that's. That is the one. That's the number one thing for me. It's like houses and that feeling when you walk in of pride or shame versus, like, all that interplay. Yep. [00:29:35] Speaker A: It's so interesting you bring that up, because I. I had never felt that until. It was about a month ago. It was the day after Isabella's birthday party, which went so well. It was. I felt really inspired. She loves Moana. We did this whole Moana theme. I hired a Moana to, like, come and visit. I made all the food, and I made it, like, Moana themed. It was like this Polynesian style thing, and it was great. And, you know, all our friends came and it was beautiful. And then the very next day, we went over to a friend of mine's house from college who I'm doing some work with, and he just had it, like, at his house. And I walked in this house, and it was. It was that, like, voom. Like, oh, my God. Because it was. My God, like, it's not everyone's aesthetic, but there's this aesthetics that's like this. This modern, like, really clean lines and, like, the glass and the wood and the, like, black metal sort of thing. [00:30:18] Speaker B: Yes. [00:30:18] Speaker A: It was like a house out of my dreams. And I was like, oh, my God, this is beautiful. And, like, my wife and I live in a three bedroom condo, which I love for different reasons. Like, there's a great community. Like, you know, every day there's these friends that come by with. To go play with Isabella. And like, that. That does a lot for me, that. That there's that community there. And I feel like that's important for general happiness for everybody. But, like, my God, walking into this house. I was like, oh, my God. And it. There were just rooms on rooms. And I thought, oh, there's another room over here. And that. It was decorated at the Nines. And, like, they had all this beautiful catering and all these people there. And it was, oh, my gosh, beautiful floors and this huge, beautiful kitchen and this backyard. And, yeah, I. I found myself feeling those sorts of feelings that you're describing of like, oh, I want this. And, oh, am I. Am I like, a bad provider if I can't give this to my family? And I. I was looking it up on Zillow afterwards. It's this. Yes, yes, $3 million house. And I'm like, oh, my God, $3 million house, right? And, yes. [00:31:08] Speaker B: Yeah, it can screw you up. Yeah, it can. [00:31:10] Speaker A: Well, so. So, like, going through, you know, but I've been really. I've been really focused on this idea of, like, releasing subscribers. And so for me, it. Like, I noticed it right away of, oh, this is a subscar. Like, there's something here that. That, like, you know, let me just kind of sit with this. And sit with this bad feeling. Because the classic thing, the way that these sorts of feelings become Samskaras, from my understanding of it, is it feels bad, and so you kind of tamp it down and you're like, oh, this feels uncomfortable to feel this way. Let me just, like, you know, reigning in the dragon, where we're going to put the dragon in a cave over there, but then it just kind of feeds on itself, and then it comes up in weird ways. And so for me, what this looked like is just really deeply feeling, like, what am I feeling about this house? Is it envy? Like, do I want to live in that? Well, no, actually, I don't want to live in that house. I just thought it was really beautiful. I'm like, I. I actually feel happy for him that he lives in the house. Like, and it's great that, like, we can go over there and hang out with him. And I love that, like, I have this relationship with him that I can go and hang out at his house. And actually, I. I love the house that I'm in. And what is it about? You know, it was really clean. I think that's. That's a big part of it. [00:32:09] Speaker B: Okay. [00:32:09] Speaker A: My house is kind of messy right now, and I'd like. And so I spent the day kind of tidying up, and I was like, oh, actually, I feel a lot of that has released now. What else is there? Let me. Let me, like, really feel into this Deeply. And it's that. It's that sort of process soup. [00:32:21] Speaker B: It's not one ingredient. There's a whole bunch of stuff in there. [00:32:23] Speaker A: Yeah, yeah, yeah. That ties in with a lot of stuff. But the fun thing is, like, the more I've been practicing this and the more that I release the subskaras and just feel them deeply, the more nuanced that can be. And the. And the. The less pronounced it is. And it used to. I remember, like, maybe just five years ago, it would just kind of hit me in this way that I wasn't even acknowledging it. It would just be this sensation that would kind of color my whole reality. Talking through how I feel about customer support emails with Dave, there's so much nuance to it. It's like, oh, there's, like. There's more heat on my right side than there is on my left side. That's so interesting. Whereas five years ago, I didn't. I didn't notice it in any sort of detail like that. It was like, oh, it just feels bad and I don't want to do it. And I wasn't even kind of aware of my own body. It just. It just felt like a thing I didn't want to do. So, yeah, like, it. This. It feels like I'm moving in the right direction and feels like this framing of, like, releasing some scars and feeling things deeply and paying deep attention to myself is the. Is the way through it. [00:33:11] Speaker B: It's good. What I have done over time is basically admit that I can't ignore it and. And I use it. So it is the envy. It's a weird thing to say. Envy is the key ingredient in my motivation. That's it. I have to just be okay with that because that's the truth. My. My nature. Remove all of those factors. My nature is. It's not lazy. It's just more relaxed and to get myself into a motivated place. Yeah, that's the thing that does it. So I. I try to admit to myself that I'm imperfect and that I have an envious nature on some of these things, and I use that as fuel. So when I take my walks, I enjoy. Instead of getting this emotional pain of envy, I enjoy walking. I live in this neighborhood. 2. Two streets away is like the fancy street, and I end my walk there. And when I'm at a weaker place or I'm not viewing things properly or in a healthy way, I lust after what I'm seeing. This beautiful house. Oh, my God, I want it. How come I'm not there? How come I'm not good enough to do that? Shouldn't I be there by now? All that crazy internal dialogue. [00:34:25] Speaker A: Yeah, yeah. [00:34:25] Speaker B: But when I am using it properly and in a healthy way, I view it and I say, maybe, but will have a house like that one day. But this is my neighborhood, right? [00:34:37] Speaker A: Yeah, that's. The house are like two streets over. [00:34:39] Speaker B: Yes, yes. Like, don't forget I live here. Yeah. This is my neighborhood. [00:34:44] Speaker A: Yeah. [00:34:45] Speaker B: And then I go back to my house. I'm like, huh, lovely. Very happy. And it's very helpful for me to almost think, like, if things go well and this thing happens and let's say Rosie sells and would I move? And a lot of times I'm like, I don't think I would move. Yeah. I do a little work here and there, but it helps, like, calm me down. But I will tell you before. Before I got to this place of having this house or the prior, whatever it was, it was relentless. That internal dialogue was exhausting. And the only thing that quieted it was being able to just move up to a level that I could argue with myself or almost. I didn't have an argument with myself because if I applied any wisdom at all, I would look around me and be like, what. What are you complaining about? [00:35:32] Speaker A: Yeah. [00:35:33] Speaker B: Yeah, right. So. [00:35:34] Speaker A: But. [00:35:34] Speaker B: But that. [00:35:35] Speaker A: That's interesting. The way you're framing it. Sounds like you've. You've. You've put a harness on the dragon. You've tamed him a little bit to kind of keep me going. Yeah, yeah, yeah. What's. So I think. I think I used to have a fear that, like, if I didn't, I had the same sort of thing going on. It wasn't quite driven in envy, but it was, ah. It was like a. [00:35:53] Speaker B: It was more of a. [00:35:54] Speaker A: A superiority thing of this idea that, like, I'm smarter and better than other people and I need to. I need to like, enforce that narrative. And that's. That's what's keeping me going. And I think I had this idea that, like, if I let go of that, I would all of a sudden become a useless piece of shit. That I was like, if I'm. If I'm okay and I'm not being driven by one of these demons, like, what does that mean for me? Am I gonna. Am I gonna stop contributing to society? Like, that's. That's what's driving me to. To go and. And improve things and make things better. And what I've realized is, like, I had so much less control over what was going on than I thought I used to. I think I. I think I had this, this image of, like, I'm. I'm holding onto this thing and it's, and it's driving me and that's what's making everything happen. But, like, I don't, I don't control it. I don't. The sun is going to come up tomorrow and I have zero impact over that. Like, yeah, there's. There's things I can be doing to make things better and, you know, I can be improving the world through file inbox and through different work than I'm doing, but how much control do I really have over that? Like, I, I didn't get to decide that I have this ability to, like, make software and understand it. That a lot of that's kind of predetermined genetically and like, the situation that I grew up in. And I didn't, I didn't decide what school I went to or like, what mentors I had or, you know, the concept of a computer, I had nothing to do with that. [00:37:00] Speaker B: That just. [00:37:00] Speaker A: This is the world that I kind of got dropped into. And so releasing even that has been instrumental and I feel like has helped me embody more what you're, what you're talking about of, like, this more calm state where there's this more relaxed part. [00:37:12] Speaker B: Stop yelling at yourself. [00:37:14] Speaker A: Right, right. That, that, like, I can just be more in that state and it's actually fine. Things still happen and I still get things done. It's just that I've kind of released my idea of how things are supposed to go or have to go in order for them to be okay. So, like, being open to it might not happen exactly how I was thinking it happened, but what the hell do I know? I don't, I don't know what the. Maybe the best version of the world is that this woman's wedding was ruined because that meant that, like, I don't know. Yeah. Who knows? Fast forward five years and actually that's the best way it could have gone. Yeah. I have no idea what's happening. I'm not in charge of the world, but, like, I can just kind of be in the groove and accept things as they are and, you know, work to make things better without. Without being tied to a specific version of what I think. [00:37:56] Speaker B: Yes. [00:37:57] Speaker A: Is the best way. Yes. I think it's a good way to put it. Right. [00:38:00] Speaker B: If you tie yourself to some, like, concrete goal number, place to be. [00:38:04] Speaker A: I'm going to be in the $3 million. [00:38:06] Speaker B: Yes. [00:38:06] Speaker A: Yes. [00:38:06] Speaker B: Two blocks away. [00:38:07] Speaker A: Yeah. Yeah. [00:38:07] Speaker B: It's like, that's not how life works. A little looser. [00:38:11] Speaker A: Probably better. Yeah. Yeah. [00:38:12] Speaker B: All right, so let's go back to this week. [00:38:14] Speaker A: Let's go back to this week. [00:38:16] Speaker B: On Tuesday, we have standup, whole team, six of us. Right. So we do weekly. And this. This week on Tuesday, we did a postmortem, retro, whatever you want to call it. We had an incident happen on Friday of the prior week. [00:38:36] Speaker A: Was that the AWS outage? [00:38:37] Speaker B: No, no, was not. It was totally our fault. [00:38:40] Speaker A: Okay. [00:38:40] Speaker B: Not unrelated to aws. [00:38:42] Speaker A: Okay. [00:38:43] Speaker B: So no need to get too into the details of exactly what happened, but we messed something up. We have a pilot going with a big potential customer. Hundreds of locations for their franchise would make a very big impact on revenue and credibility and next opportunities, all that stuff. So very important. One of the big priorities in the company is to get this pilot to be successful and for them to convert and then for that to lead into new opportunities. [00:39:10] Speaker A: Great. [00:39:11] Speaker B: We screwed some things up on our way to replicating all of their accounts. It's one thing to go in and manually create an account on your own, create a username, password. Different thing for us on our end to deploy something that creates a hundred accounts for one, like master account. [00:39:28] Speaker A: Okay. [00:39:29] Speaker B: Also, less transparency. Right. You kind of don't see that process the same way the engineers see them, but the rest of the company doesn't. In that process, we missed something. [00:39:38] Speaker A: Okay. [00:39:39] Speaker B: We had a feature flag that was off and should have been on. So we're a few weeks into this pilot, and we realize that feature isn't even on. So the potential customers coming to us and saying, man, this really dropped off, you know, what's going on? And we kind of couldn't figure out. And we realized, oh, my God, we're just not. We're just not sending this part of the, you know, feature set at all. [00:39:59] Speaker A: Sure. [00:40:00] Speaker B: And it's a big deal. Is a bad mistake. [00:40:04] Speaker A: It had been going on for weeks. You said for weeks. [00:40:06] Speaker B: That's right. So we say to ourselves, okay, no need to freak out. First thing to do is fix it. Next thing to do is communicate, and the next thing after that is, let's take a step back. Let's write up our. Our postmortem, what happened, and then talk about it. So that's what we did. We fixed it right away. We put together a communication plan on, you know, the. Where we concluded on the communication is that being honest is the best thing always. So let's just be completely blunt. Here's what happened here's why we're sorry. This is how we're. What we're putting in place so that it never happens again. But it was entirely our fault and we apologize and that's what we communicated. We have screwed things up all the time. Like, like other software companies, we almost always default to brutal transparency. I think it ends up building more trust. Anyway, we don't even like the sugar coat. We're like, this is where we messed up on this date and this is what happened. So. Okay, well, I think we're used to that from the checkout payment sort of thing because there's no hiding like you just the people need to know it has to do with payment. So I guess that's our default. So on Tuesday, we have this stand up and we get into it and we spend 10 to 15 minutes talking about these issues and these mistakes and what happened and why. And then I could sense everyone was done talking about it, but it, the topic wasn't done, but everyone was like, had had enough of being uncomfortable because, you know, this is uncomfortable. You know, you did this and I did this and why would this happen and how could you do this and how about this mistake? And I pointed this out three weeks ago, but you didn't listen to me. You know, it's not like a fun conversation. And I had a choice in the moment on whether to let it go and then take some of these conversations that still needed to be. Needed to happen, but take them into DMs and outside of the group setting. And instead I, I basically said, we're not done talking about this. I want to go deeper. And then I kind of facilitated discomfort. Sam, you said this. Do you still think that's right, given that Andrew just told you this thing? And I like, forced these uncomfortable conversations and we kind of just hung out there for another 30 minutes and it. I can't help but liken a lot of startup and team issues to my marriage and relationships. [00:42:20] Speaker A: That's exactly what I was thinking of you. Yeah. [00:42:22] Speaker B: Because you can go a while without having hard conversations, but the longer you go, the more resentment builds and then the worse the conversation will be and the more damage it can potentially do because you've waited so long. And then the more difficult it is to repair back to a good place. And at a company level, you don't owe people you work with the same thing. You owe your life partner, your wife, your spouse, husband. So it's easier to avoid hard conversations. Whereas in your marriage, you're like, you know, I don't Want to walk around the house mad at each other for any longer? Let's just have it out. [00:43:03] Speaker A: We're going to figure out where the teaspoons go, Doc. God damn it. [00:43:09] Speaker B: The space to acknowledge pet peeves is huge in marriage. I absolutely. It's almost like, do you have one? I have one. You want to say yours because I want to say mine. Yes, we do that regularly. So that's what it felt like on Tuesday. It was this big, difficult conversation and we kind of kept going and made it more uncomfortable and said all the things. And this week because of that had a weird vibe. It was like feelings were hurt all over the place and communication was impacted. Like you can kind of sense in these slack conversations some discomfort, some anger, some sharpness. And I had a few one on ones later in the week and I had an unscheduled one on one with a team member that basically reached out and was like, can we just talk about what happened on Tuesday? And what this team member had told me was that they're not good at responding in the moment and they like to process things. And she wanted a day to process before she talked to me. And I was like, respect for understanding yourself that way and respect for reaching out and saying, I need to know more, I need to talk about this more. I need to understand where you're coming from. So it was like a. It was like a week with a fight in the relationship and we're working our way back and I am confident that we'll be better off for it. But it felt, it felt uncomfortable, it felt a little dangerous. If I'm being honest, as the boss, I felt this danger around. Did I push too hard? Does that lead to people thinking about leaving? Does it make them unhappy at their job? Did I, you know, so all those questions kind of opened up overall, you know, it's a few days later, now it's Friday. This was back on Tuesday. I'm happy we did it. I don't even know if, if happy we did it is important. It needed to happen. And I think we have a path of the next week or two and beyond to change some habits and patterns that led into this mistake. And like in a relationship, if something happens, someone says something, does something that you're. You're talking about that. But focusing too much on the individual thing that happened, it's almost not, it's not the right perspective because you're talking about, well, this happened. Then you said this and then I said this and this. These are like the facts of the case. When in reality you got there based on this history of other things said and done. So it felt like people on the team were asking me to understand, like, what happened on Friday and that deployment and this is what led up to it, and this is why this person missed it or I missed it and this is what we should do to fix it. And I was like, that's actually not a big enough perspective on. On the conversation. I want to look back at the last few months and how we've kind of gotten into this place that could happen. But I don't want to just focus on the facts of this individual incident because that's. That's not enough. And that felt dangerous because that was not like, well, here's this one thing that happened. Let's figure it out. It was like, how are we working together? How do you need me to change the way I work and communicate? How do I need you to change the way you work and communicate? Bit of a high risk, high reward kind of set of interactions in the company. I. Yeah, from my check ins with people, I think people are okay and that they're happy that this got brought out, but it is not without some scar tissue being built and some damage. And it takes time to build up that confidence and love and trust back to where it was. Yeah, it was. It felt difficult. On top of all the other things that are difficult, we normally don't have very much people drama, which I think can be one of the most difficult things in any company. But we have six people. We've kind of been through some shit together. These are the six people left from, you know, 20 people that we cut down to six from the previous product. We built this thing. It's going well. Doesn't mean it's not without its challenges, but it does feel like a tight enough circle that we can kind of, you know, keep holding hands while we're yelling at each other. [00:47:08] Speaker A: Yeah, yeah. I'm reminded of a few things. The first one is the last time I talked, I think you were remarking on how well things were going and how smoothly the team was operating. And it's easy to do that when, you know, revenue is growing. And I think at the time you're growing by like a thousand dollars a month more in mrr and that there was group cohesion. But the test of a relationship, the test of good company cohesion is when things are going badly. And yeah, it's not fun. And yeah, it is dangerous when you're having this sort of conflict. Yeah, people can leave. I remember Distinctly the moment when Sarah and I were first dating. The moment when I decided, like, I can say she asked me a question about. She was like, hey, you seem like you've been really distant. And this was after we'd been dating for, I don't know, a month. And I had a choice in that moment of like, well, I know the right thing to say. Here is the right thing. Meaning, you know, the thing that'll, the thing that'll go the easiest is like, oh, no, I haven't been distant. Like, I'm good. I don't know what you're talking about. I'm a little off. Yeah, yeah. And like, there was a second where I was like, no, I'm going to decide in this relationship, like, I'm going to make the more dangerous choice. I'm going to confront this head on and see what happens. And I was like, yeah, I have been feeling distant and I don't know why, but like, it might, might be because this isn't this. You have a cat and I'm allergic to cats. And I'm thinking about, like, can this work out between us? If you have a cat, it's me. [00:48:17] Speaker B: Or the cat, right? [00:48:18] Speaker A: And that led into a fight. And it was, it was the first fight we'd ever had. And it was a high stakes fight. That was a fight that like, could have ended the relationship. And at the time, like, that, that was a very risky move for me because I really like this girl and things are going well and I'd like to kind of play it safe. And I had recently there was a therapy session I was in with the co founder who fired me actually, but he gave some advice which was we were having a conflict at the time of around timelines. Laura, my, my ex co founder would say something like, you know, here's this feature. How long do you think it'll take? And I was like, I don't know, I think it'll take like three or four days. And inevitably it would take like two or three times that long. And that was just a repeated conflict that we were having. And the way that he framed that for me was probably Christian. Within you, you're wanting to avoid the conflict because, you know, you're wanting to give her more of an optimistic estimate for how long things are going to take. But there's going to be pain either way. Either you can pay the pain now, disappoint her now and say, actually that's going to take like two weeks, or you can defer the pain, pay it later, but if you pay it later, you're going to have to pay interest. [00:49:18] Speaker B: Oh, that's a good. If I was going to say it's cheaper to do it now, but I think interest is actually a better concept there. [00:49:23] Speaker A: You pay interest on it and that's a framing that's just that stuck with me. So it sounds like in the conversation, you know, after, after people kind of had enough of it, you were choosing to front load more of that. But then the other thing that comes to mind is in couples therapy for Sarah and I, a really important element of conflicts Sarah and I have, that's been recommended now from, from different books that we've read and two separate couples therapists. Is this, this idea of a timeout that like once you, once one or both of you get to a point where it's no longer really about the thing, you're. You're kind of having an argument about the argument. That's the time to take a step back and say, okay, we're going to take a little break and we're going to kind of let things air out. I love that one of your employees took the data to kind of like let things process and that they were self aware enough to know that that needed that. That's the same sort of philosophy. I feel like that comes with the timeout. Yeah. So it sounds like it went reasonably well. And conflict isn't fun, but I think it's necessary. And this is like, I'm so much more interested in examples like this as opposed to like, ah, we're making so much money and closing all these deals and everyone's having a great time. Well, okay, it doesn't matter. Like you could have a terrible company structured and terrible relationships in it and still be feeling the same way. Like the test of whether or not things are really going well I feel like is moments when you're tested like this of when stuff's going wrong and how well do you actually handle conflict and how do you resolve that? How do you repair afterwards in a marriage? You can just have sex. You can't do that. Different. [00:50:38] Speaker B: Can't do that. No, no, no, no makeup sex. Nope. Right? [00:50:41] Speaker A: Yeah, yeah. [00:50:42] Speaker B: It's, you know, to bring it down into like software development. Right. Because that is the, that's why it's so hard. Software is really hard. And, and building software as a team is really hard. And this like separation of responsibilities between who's building, who's selling, who's servicing, who's supporting all that, it's really complicated. But that concept you mentioned around expectations. A lot of it starts there in the development process and in the setting of expectations. And one of our, our problems is that we're very busy. And so there are always very valid excuses. And the problem with valid excuses is they impact the people involved differently. So what I mean by that is when an engineer says, I'm going to have this ready for the pilot, I'm going to have this ready for the features, whatever, I'm going to have this ready on Wednesday. Then the person who is communicating that to the customer in their mind says, okay, I'm expecting it on Wednesday. I need to start communicating, making promises, setting expectations with the customer. Then the engineer goes through and is doing, working all day, but doesn't finish the task on Wednesday. But, but valid, like busy and I'm pinging them and can I get this? And what about this thing? And then support thing comes up and something unexpected happens. And what we're trying to adjust as, like a real practical adjustment is when a promise is made, it's up to the person who made the promise to communicate. So it's not okay for the salesperson to come back on Wednesday and say, so is it ready? Because you told me to be ready. It's on the other person's plate to understand and have in their set of responsibilities that it either gets done on Wednesday, or if it's not going to get done on Wednesday, you communicate as early as possible that it won't be done and explain why. And just that slight shift in onus on who's responsible for that communication is something that we need to do because otherwise then someone's always chasing and then that's just an unhealthy version of communication. So, so is it gonna be done by the end of the day? So, so it's the, is it done, have a tomorrow, you know, so you're kind of pulling. Is the lesson I remember my dad taught me early on was when you borrow money from someone, you pay them before they ask you, kind of like same principle, don't wait for them. That's it's not on their responsibility for them to come to you and say, so you have that 10 bucks you owe me. Like, that's a fundamental misunderstanding of where the responsibility lies. So we're trying to do that internally. And it forces both sides to improve because what it also does on the engineer side in this case is it forces them to take the path of the cheaper without interest payment, because you're always, always better off saying, oh, this is not going to be done. On Wednesday and here's why. Here's what I have and if you want it done on Wednesday, I'm going to put my elbows up and I'm going to create space and I'm going to say, no, I will not answer you, Jordan. No, I will not get this to you. I have another set of responsibilities and promises that have already been made that I can't be moved. And so I'm going to ignore slack. I'm not going to pay attention to the billing channel, I'm not going to pay attention to the support channel because I'm shifting my responsibilities. So we're trying to create this space from these mistakes. [00:54:12] Speaker A: This is such a universal problem. I feel like in software development that I'm so curious to hear how this works for you. If that's because Laura and I sort of landed in a, in a similar position of like, yeah, communicate more in the moment, like be sending her more frequent updates and also, you know, be, be more conservative with my estimates. Like if I, if I think in my head something's going to take two days, you know, say that, but then also think more out loud of like, okay, so if I think it's going to take two days, if I'm also doing all this other stuff, it'll probably take a few more days. And I think that's, that's certainly a way that it could be improved. However, I think this is just fundamentally a really hard problem. I think the, the way that I'm framing it now, hearing you talk about it, is it's sort of the, ah, it's, it's a mismatch between two different modes of work of like on one side it's this kind of predictable, managerial, like we're talking to this customer. You want this thing? Let me go get the thing. It'll be ready on this day. Okay, it's ready on this day. Like it's very email kind of predictable, transactional sort of thing. And the software development side, which is the world that I love inhabiting because it's so like creative and open and sometimes you get these problems and you're like, oh, I think this is going to be pretty easy. But you open the box to do the thing, you're like, oh my gosh, actually there's this whole mess in here and I need to like organize all these tools first and do this thing first. And the thing that you thought was going to take you an hour actually takes you like a week to do it properly. You can kind of put band aids on it. But the more that you put band aids on it, the gross. This machine gets grosser and hairy and all these interdependencies and then all of a sudden the whole thing grinds to a halt. So it's really this. And it. My God. One of the reasons I love software development so much is I feel like it just takes all of me. It's. I gotta take the whole thing in my brain and it's just. It's really. And then it's verifiable when it works. And so the difficulty that I have from the engineering side of that, when I was giving the source of estimates to Laura, is like, to be totally honest, I don't know how long this is going to take. Like, this is a new thing. I. Based on what I currently know, based on where I am right now, I think it's going to take two days. And my margin of certainty on that is like, it might be immediate, it might take. It might take a month, it might be impossible based on some of these other constraints that we have. [00:56:10] Speaker B: It's brutal. [00:56:10] Speaker A: And so, yeah. And like to be trying to be inhabiting that space, this feels sort of arrogant to frame it. But, you know, I'm imagining myself sort of like painting this painting or making the sculpture. [00:56:20] Speaker B: Like, don't rush. [00:56:21] Speaker A: It's really hard to like, fit. Right. Like, this is hard. This is hard. And it's very. It's very. It's a different sort of work than the sort of work that you're doing. Not to say that my way of work is better. It's a different. It's a different frame of work. [00:56:30] Speaker B: Yeah. [00:56:31] Speaker A: You're doing things that are like, how long does it take you to write an email? You can say with pretty close certainty. It's going to take like between 2 and 10 minutes. Very rare that you have an email that takes you more than 10 minutes to write and that's like very predictable. But in this more creative domain, it's like really hard to get a handle on these things because it's ethereal and it's like all these abstractions and it takes your whole brain to be able to do it. So, like, yeah, fundamentally I feel like this is a very different problem. So I'm curious. I'm curious if this helps it. And I see this as a perpetual problem, just like in the industry, that this isn't. This isn't a thing I've seen a good solution for. [00:56:58] Speaker B: That's right. And it is really a fundamental misunderstanding of the way this works. To expect the non technical side to look over at engineering and say, well, you know, do it better or do it differently. In reality, it's like we need to give more permission to the engineers to say, back up. I need space, I need time. And if you expect me to react to every support ticket as soon as it comes in, you're going to get nothing from me. And when you get anything from me, it's going to be. It's going to be the Band Aid, it's going to be the quick version. So give me the space and empower me to create my own space. We happen to have an inherent advantage, at least I try to frame as an advantage. We are half us, half Europe. What that means is at the beginning of the day in Europe, we're asleep. I see that as an opportunity. Ignore slack, ignore everything. Ignore anything that would be reactive and bask in the glory of how lucky you are as a software engineer that you get to work on a product that's growing like crazy and no one's going to bother you because everyone's literally asleep. That's when you do your tasks and create your space instead of trying to get ahead of things and make support happy by having it ready by the time they come in. Like, no, no, no, no, don't do that to yourself. Take more time and more space to do the, the actual engineering work. Because where we are right now, those first few months when you don't have customers, it's like this pure engineering field to play. Yes. At this point in time, there's chaos because of the customer. So it's like the success created the chaos. Now you can't let that impact the success. It reminds me of, like, the sales and it's like the, the SDR versus the salesperson. You can't have one do both, because then the more you succeed as an sdr, the more sales you do, and then you're punishing yourself as an sdr. So you really do need to separate them. And this is like a, you know, I don't know, one layer up from that where you're like, don't let the engineering get swallowed by the success of the product that now needs support and success and all these other things that require engineering to be involved. In theory, it'd be great to silo and you only work on features, but it is just not like that because the person who built the feature is actually the right person to help with the support around that feature. So that's what we're going to work on over the next few weeks is this how do we create the space, these pockets of focus for these three hours? Just ignore slack. This is partly why I think 37 signals is so important that it exists out there as this like freak phenomenon. [00:59:37] Speaker A: I was about to bring them up. [00:59:38] Speaker B: Yeah, because they, you know that that's what they preach. Their preaching is like, you're gonna get garbage if that's the way you work. And I mean, they're right. And I, I always make the excuse of, well, if I was making, you know, $50 million a year with $40 million in profit, I'd have a lot of space too. But that's, but, but that's, that's again, it's a misunderstanding of chicken before the egg. [01:00:00] Speaker A: Yes. [01:00:01] Speaker B: One of the reasons, not the sole reason, but one of the reasons that they are so financially successful is because they demand to work in this way. So whatever excuses we're making are excuses. [01:00:11] Speaker A: Sure, yeah. Much, much more about the philosophy. The thing I was going to bring up from 37 signals is I think in their book Shape up, they have this concept of a hill chart of like, it's the best visual representation I've seen of this core fundamental problem in software development of like you don't know how high the hill is. You don't know when you open up the box how messy it's going to be. And so to, as a, as a way to communicate from the engineer to the non engineer or support person or whatever, here's where I'm at in this. I'm still working my way up the hill. I don't know how tall the hill is yet as opposed to. Okay, I know I've been working on this for four days and you've seen no progress, but I'm actually at the top of the hill and it's all like really reasonable from here. So my estimate from here is going to be really accurate. That's an element of it that I've seen. And then I was going to say also the, the built in time because there's that time zone mismatch. Your customers are all in the US too. Right. So it's not even like you're getting new support requests. [01:00:58] Speaker B: Nope, all us. [01:00:59] Speaker A: Almost entirely all us. Yeah. Yeah, great. [01:01:01] Speaker B: Some Australia here and there, but like it's like 95% perfect. [01:01:04] Speaker A: So. Yeah, having, having that uninterrupted block of time for the engineers in the beginning of the day, that, that feels like a good component into, into solving this problem. But yeah, I'm, I'm really curious to see, you know, where are you after these changes and what other problems are still there? Because actually I, I said there were no examples that I've seen of people solving this, But I think 37signals does it pretty well. I'm due to reread their books of, of how they set that up, but yeah, I'm curious to see where you find that balance of, of. [01:01:30] Speaker B: We really liked Shape up and it impacted especially our, our head of product, VP of product. Now when I ask her how long things are going to take, her responses, I have no idea. We haven't got into it yet. Yeah, I'm like, yeah, yeah, you're right. Yeah, that's, that's a better answer. That's a more accurate answer. [01:01:46] Speaker A: True. [01:01:46] Speaker B: Yeah. I feel like we can go on forever, but we're over an hour combined with the private podcast ahead of time, you know, we've been having all day. [01:01:53] Speaker A: We'll do another one soon. Cool. [01:01:55] Speaker B: Always a pleasure talking. Thanks for joining Marquez.

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