Two Different Approaches

[00:00:00] Speaker A: I had a good laugh today. I was listening to the mostly technical podcast and they were doing the read. Have you listened to it by chance? [00:00:07] Speaker B: Yeah. Oh no, not today's one. Not today's one. Not today's one. [00:00:10] Speaker A: So they go to do the bento read. I think Aaron goes, whatever is on my website. Because that's what, that's what you told them. [00:00:21] Speaker B: That's what I put on. Yes. Yeah. [00:00:23] Speaker A: So then he goes to your website and he goes, bento is the solution for. Right. Basically, what's on your site. 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. I am Jordan Gall, your host and today I have my longtime friend but haven't spoken in a while, Jesse Hanley. [00:01:00] Speaker B: Welcome, welcome. Not welcome, but hello. It's good to, good to be on the off site. [00:01:06] Speaker A: We haven't spoken in a while, but I still feel like it hasn't been that long. I mean, it's been years, but. [00:01:12] Speaker B: But spiritually connected, Jordan. Yes, spiritually connected. [00:01:16] Speaker A: Do you, do you remember how we met? I remember it like very, very distinctly through. [00:01:22] Speaker B: What is it? Aussie supplements plugin on like the E commerce store, right? [00:01:26] Speaker A: Yes, yes. It wasn't Transparent labs. What? [00:01:30] Speaker B: No, just wait, just wait, just wait, just wait. There was a few. That was a. That was a bit of a crazy, crazy start to my journey. Yeah, it was all these subs and I was like, what was some of the other brands? We had Femme supplements. We had Predator labs. We had natural distribution. We had. There was a lot of companies. [00:01:47] Speaker A: I don't, I don't even think it was on Shopify yet. Maybe you were on Wukai. [00:01:51] Speaker B: It was Woo. It was Woo. Yeah, it was Woo and Magento. So we had this like Woo and Magento set up. The Aussie supplement store was like ranked number one in Australia for like gold standard way Cellucor C4. All like the main supplement skus like first page for protein powder in Australia. All that kind of shenanigans. And it was just on this shoddy woocommerce store that was like barely up on site ground. [00:02:17] Speaker A: And this is what like 2014. [00:02:21] Speaker B: This was 2012. A long time ago, man. 2010, I left school. 2010 was my final year or I left school and then a few years Trying to be a personal trainer. And then after that. Yeah, it was I think 2014. 2014, 13, I think. Yeah. [00:02:39] Speaker A: So you want to hear my side of the story on why I remember it so clearly? So I started Cardhook by myself with the developer who was like a family friend. It was the younger brother of my wife's best friend from high school. Just randomly ran into him in San Francisco. We hit it off. He built the first version of the product. I started selling it, it started moving a little bit. I realized, oh, I need like a full time co founder. And the full time co founder that I met, Ben Fisher, who you know from back then also before we fully linked up, we, we met online and the first time we met in person, he was in LA with friends and I was in Portland and I was like, I think this might be real. I'm gonna come down to la. So I make the trip to LA for, I don't know, I think one night and I had a call set with you. So I took the call in front of Ben and his friends and it was like, it was almost an interview. They were basically watching me work and we did a 30 minute call. Yes. What a trip. Right? So I basically was able to show my e commerce expertise, familiarity with the product sell and you happen to be the person that I was on the call with. [00:03:55] Speaker B: Was that good? Was I enthusiastic? The whole thing was great. [00:03:59] Speaker A: I mean, look, we ended up co founders, right? So I guess I closed that deal. [00:04:03] Speaker B: Yes. Wow, that's a cool piece of law. I didn't know that Ron Wright's a trip. [00:04:06] Speaker A: That's why I remember it so clearly because that trip to LA was very important. That's kind of how I convinced Ben to join me in Carthook. Even though I was not technical and you know, kind of had a product at a few thousand bucks a month, that kind of thing. [00:04:22] Speaker B: Yeah. That's crazy. That's really cool. Before you pivoted to full checkout, where did Cardhook like end on like what was like the peak of cart hook as the abandoned cart plugin. Where did that peak in that story? [00:04:37] Speaker A: Okay, so here's what happened. We got it to somewhere in the area of 5k a month. Like when I, when I was meeting you, it was pretty early on, we started doing integrations, right. Magento, Woocommerce, Volusion. That's where I started. So that was the first one. Yes. [00:04:52] Speaker B: Wow, that's right. [00:04:53] Speaker A: And then we started to get demand from Shopify and I didn't want to build it, because it stripped away our differentiator. Back then we had, we had the ability to capture the email as soon as it was typed right on the Blur event. And that was a big deal. [00:05:09] Speaker B: Right. Because. [00:05:10] Speaker A: Right. Only the really expensive ones were offering it and we were offering it for a reasonable price. And Shopify stripped it away because it was only API based. You couldn't put JavaScript on the checkout. Okay. That is what initially had us bump into Shopify. And as we were looking at the integration there, that's when I started to basically be frustrated with the Shopify checkout, saying, you can't do anything. If I were a merchant, I would be so frustrated by this because I had just come off my E commerce experience at Volusion where I optimized the hell out of our checkout and it made a huge difference. And that's. That was the light bulb moment of, damn, I bet there's demand for a customizable checkout on Shopify. [00:05:49] Speaker B: Wow. Okay, cool. And then that threw you down that path. Okay, cool. [00:05:52] Speaker A: That's right. [00:05:52] Speaker B: That's right. Yeah. [00:05:54] Speaker A: You know what allowed us to do it? I want, I want to ask you about, about this. So the only reason we were able to do it, we were a small team. We raised a few bucks from friends and family. You know, four people had like a hundred grand in the bank. And I was like, all right, how do we make this work? The only reason we were able to do it is because we did an integration with cratejoy. Remember cratejoy, I think, subscription platform. And they built us into their product. So we just grew without any effort. So we went from like 10k months to 20k a month without doing any work on the abandoned product. And that's what it gave us, the space to build on the checkout product. [00:06:28] Speaker B: Yeah. That's crazy. Like, something I was, I was about to say before, I'm like super nostalgic for that era of app building and product product building, like the 2015s. Right. Like, there's something really nice about that era where, yeah, you could get a really good integration and have a business be built out of it. And we were still kind of exploring and everything was kind of, I don't know, everyone was trying to like, figure it out. It was a little less fast moving and noisy than it is now. But yeah, I've been thinking about that a lot lately. It's just like the 2015 was like a really unique year. And a couple of years after that. [00:07:01] Speaker A: I think everything felt very reachable. I don't Know how to describe it was like, okay, someone wants us to do a crate to integration. And I was like, I'll be right back. I'm going to find the founder, you know, and then like 48 hours later, I'm on a call with the founder. Everything was kind of within reach. You could go onto Twitter and just tag someone and they would reply to you. You could email them and they'd reply. It was like toned down. It was less noisy, I guess. Is that the word used? [00:07:30] Speaker B: Yeah, I mean, like the, yeah, the main differentiator was like, if you did something, like, if you did, stuff would happen in that era. Right. And if you, like, if you made landing pages, if you built like all that kind of stuff, like if you actually put in the work and the work was kind of. It was obscure. We didn't really know what the work was. So then you'd hang out on growth hackers.com and like all those Mixergy. [00:07:53] Speaker A: Mixergy. [00:07:53] Speaker B: Mixergy. You listen to a mixergy interview and then someone would be like, you know, like, I do these things on SEO. I mean, a lot of the SEO stuff that we, we did back on the supplement site was like me reading Viper blogs and learning about link stuff and doing all that exploration. And I, I just, I, I would listen and I would do the work and then stuff would happen. And that, that was the main differentiator back then. It was just. You just had to do what you read about. But now there's like, there's so much content, there's so much people saying stuff, and just because you do doesn't necessarily mean it's going to work. And, and, and arguably the doing is getting so much easier. Like even coding, coding is a lot easier to do now. Everyone can code. But that's still, that's now not the differentiator, the, the doing the work. There's a lot more now, which I think is kind of interesting. Yeah. [00:08:41] Speaker A: And, and some of the notes I have for this conversation are centered around this concept of like, longevity. You've been doing bento for a long time. How long has it been? [00:08:53] Speaker B: Probably four years full time, and then maybe like three years. Like faking it, maybe faking it or. [00:09:00] Speaker A: Or juggling multiple projects because. Right. [00:09:04] Speaker B: By the agency, right? Yeah, no, I had the agency. The agency was paying all my hotel bills as I was traveling around the world. So I kept the agency and exited the agency in covert. And so I sold that actually to some customers and friends. And so they, they acquired the agency and then I went full time on Bento, basically after that I always had like some personal stuff, like I lost a child around them as well. And so I kind of grief built Bento, if I'm going to be really honest. Like I spent basically a year coping and coping actually brought Bento to life because that was all, that was all I worked on, something to focus on. Yeah, it gave me something to focus on. It gave me something to control. I think that was, that was a really big part of it. Like I could control Bento, whereas I didn't feel like I was in too much control of my life at the time. And that, and that, that actually got me through a lot of the grieving. And then after that, after like that first year, it was like Bento was only doing like a few grand a month or whatever. Right. Kind of like cardhook. And then I really focused and when I focus, it just, it just went up and, and now, and now we're like, you know, single digit millions and it's just me still with a part time support person and a part time guy in design for, who helps me with docs. [00:10:18] Speaker A: Okay. You, you just covered so many things and there's so many questions in between all the things. First, I'm very sorry for the experience you went through and you know, I'm sure with hindsight now you kind of view it differently, but it's interesting to hear that work was an outlet for it and the work we see now in Bento, that, that, that was the outlet. [00:10:39] Speaker B: Yeah, it was, it was, it was. And for what it's worth, me and my wife try it again. We've got a beautiful 3 year old daughter who I spent all this money with. So, you know, life, life figures itself out. [00:10:49] Speaker A: But yeah, you've managed to arrange a relatively unique life. [00:10:54] Speaker B: Yes. [00:10:55] Speaker A: Right. I mean you, you're from Australia and, and you ended up in Japan and I don't think that's very easy to do. Immigrating into Japan and living there full time is not like a simple thing is my understanding. [00:11:06] Speaker B: Yeah, no, it's. So ever since like 2015, I've been kind of traveling around, right. And I would spend about half the year in Europe, half the year in Asia. And for a long time I was just trying to, I was kind of like shopping for where to live in a way. And then I, I came to Fukuoka and I met my now wife Michaela and she showed me Fukuoka and I just, I just loved it. It was very like relaxed. I like society here. Society's very like, you know, everyone always says this, but it really is true. It's safe. There's a lot of kind of social cohesion that keeps everything operating really well. Some people don't like that. I like that there's a lot of like social compliance aspects to it and all that. Okay. But yeah, my wife's on a long term visa and I basically adopted that after we got married and then we had the kid and stuff. Right. So we had some routes to live here. But then I've got friends in like Tokyo, they're on business management visas. Like you figure it out. If you want to live in Japan, there are parts and you can always figure it out. But it is, it is, it is a little bit difficult, but I think Japan offers, out of all the countries I've been to, the best price to quality of life. So for example, we were just talking just before, before you started recording. It's like the place that I'm in now, it's fifteen hundred dollars a month. It's in the center of the city. I've got restaurants all around me. I'm in a two story house, I've got a garden. The city parks over there. I can take my kid to the pool. 1500 bucks a month, right, for that apartment. If you were single. There are amazing apartments around me for 400 to $800 a month for a one bedroom. So, you know, so I don't think. [00:12:36] Speaker A: The idea of Japan being very expensive and out of reach is kind of outdated. [00:12:40] Speaker B: It's outdated once you are out of the tourist part. Right. So it's like when you are living a suburban Japanese life, all the costs go down. Like all the local restaurants, like the photos that I post online that, you know, we're talking about amazing food and you're looking at like $15 ahead, $20 ahead, sometimes $8 ahead for breakfast. So, so reasonable because the salaries are. Yeah, yeah. And the, because the salaries are low here, so the, the yen continues to tank. Salaries don't go up too much here. Inflation keeps getting pushed off because they keep pumping money into the country. So yeah, it's a, it's a good place to live. [00:13:15] Speaker A: Yeah, it sounds that way. And it sounds like the arbitrage of building online is advantageous. [00:13:23] Speaker B: Yeah, yeah. And then even on like the, the, the tax side like there, there are some downsides on like the tax front which we're like currently exploring. But even with the tax stuff, even with the tax stuff factored in, it's still cheaper than Sydney, it's still cheaper than the US still cheaper than Vancouver, which my wife's Canadian. We could. We could move to if we wanted to, Right? A lot of Canada. Yeah, yeah, yeah, yeah, yeah. [00:13:45] Speaker A: So now I want to get into what you alluded to before. You're still solo. [00:13:51] Speaker B: Yeah. [00:13:51] Speaker A: When I view your Twitter and I kind of see the timeline of your story over the last few years, one of the things that strikes me and I wanted to get into in this conversation is a feeling of patience. You don't seem to be in a big rush. You seem to be committed to doing good things over and over and over again for a long period of time. Like, I still see you doing a level of customer support that feels unreasonable on Twitter, but you were doing that four or five years ago and you're still doing it, so clearly it works. But I don't know many people who have that level of, like, patience and dedication. [00:14:32] Speaker B: I don't know. There's so many thoughts that contribute to me acting like that. Like, you know, part of that's like agency stuff. So with the agency, it's like you're always going above and beyond to retain clients. So when you apply, when you apply that to like a SaaS aspect, it's like, you know, I work really hard to get a client, but then there's this thing where I've kind of realized where it's like, if I help a 30amonth customer, I help a 50amonth customer. Often that bleeds into a $2,000 a month customer coming in. Somehow that's just like how how my space works. Right? Yeah. I help some, like, creator who's in Colorado and like, he's probably going to turn in two months, but then he tells an actual real business owner that has like a massive business that, oh, I had this amazing experience, and maybe he helps that person move on to bento to get paid. Like, there's all these connections. And I think acknowledging that that is how business actually gets done online makes me kind of behave in that way. And then also, I don't know, I just like the space that I'm in. So I'm in slacks. I mean, communities. I'm talking about stuff, I'm interested in stuff. And the aggregation of me just being everywhere and talking and doing stuff leads to inbound at the end of the day. [00:15:37] Speaker A: Yes, it is reputation building. And right. What it's done over time is solidified the reputation of, like, expertise with helpfulness. I guess maybe I view it as this patience thing because somewhere along the way I lost that. I did that in the e commerce world. I Did it for Shopify merchants at Cardhook with the checkout and something along the way I kind of, I kind of got sick of maybe giving too much of myself into that. [00:16:04] Speaker B: Can I give an idea on why? [00:16:06] Speaker A: Maybe I'm not sure. I'm really not sure. Maybe maybe it's because I got frustrated that I didn't get out of it what I put in. Maybe I'm pretty transactional overall in terms of like I do work for money and, and I started a business for money for my family kind of thing and I think maybe I really sacrificed and maybe there's some like righteousness about that about like how much I suffered under the Shopify issues and this thing got killed and we got the 6 million ARR and then it got destroyed and I think maybe I like protect myself and I put up some walls and now like Rosie is a reflection of that. It is self serve SMB. I don't do any support. You know, I guess maybe I needed to create some distance between myself and customers and that, and that that heat of the emotional aspect of do they say yes to the deal? If they do it's because of me and if they churn it's also because of me and like that the emotion attached to that. [00:17:13] Speaker B: I know there's, there's a lot. There's a lot. Yeah, there's a bit there to kind of unpack. I mean I think, I think there's, there's a few layers here. I think a large part is like identity. It's like who, who do you identify as and like who do you want to be like in Japan? You know a lot of my founder friends are all running successful small businesses online. Right. So we're talking you know, single digit millions or hundreds of thousands a year or whatever. Like they're just making like a, they're pay, they're paying their bills and they're doing a good job. But I don't have many friends that are making like 10 million or more or you know like these big business. I don't have any. I know no one's making 100 mil or more. I've got no one, no startups that I talk to. So from, from my sphere of influence I have no one that I want to be like if that makes sense. [00:18:01] Speaker A: Yes, yes or, or. [00:18:02] Speaker B: Yeah. [00:18:02] Speaker A: I'm sure you admire people. We all do admire people online and we'd like to attach to those people because they feel few and far between. We kind of see the people that we anti admire and we are frustrated by and all the nonsense talking and the, you know, the boasting and all, all that aspect of it. But in your social circles, not your Twitter circles. [00:18:23] Speaker B: Yeah, but also even like local, right. Even by me. There are some houses here which are extremely modest. We're just having to look at your street, which was stunning, beautiful, massive houses. There's a guy around here that has like a Lamborghini. It's like a very, very nice car. And your house absolutely mogs his. It's like it destroys his house. Right. And. And I have no idea how successful is. I imagine he's successful because he's got like a nice car and stuff, but he's. His house is super modest. It's like, I'm assuming his lifestyle, given that house is fairly like modest. And I noticed that a lot around Japan you just don't really have. There's no one I'm kind of keeping up with around here. People don't really have, I don't know. [00:19:06] Speaker A: Materialistic ambitions the same way. [00:19:09] Speaker B: So then it means on like the finance side, I don't really have any. Like, I'm. I'm far past. I'm surpassed my financial needs. [00:19:17] Speaker A: So you're post economic like Matt Monwick. [00:19:20] Speaker B: Yeah, in a bit of a different. In a bit of a different way now. Now if I was in Sydney or living in Vancouver, I can see myself wanting to be something different. And there are times where I go, you know what, Like, I would, you know, could Bento. Could Bento raise some money and hire. Could Bento 100% could. Could I start scaling up sales? Could I. Could I start doing all these things? And then at the end of the day, I decided don't want to. Like, I just. I don't know. I like how it is now. Like, this morning I woke up. I'm really just talking to you today I was with my family the most. I'll probably hang out with my wife later. Like, I don't know. It's like a. It's a good life and it's a. And it's profitable and I feel financially secure. And I think my mindset would only change if I was hanging out with different people, I think. [00:20:13] Speaker A: Okay, so two things. One, I agree that the environmental influence is very big. I feel it for people listening. Before we started the call, Jesse and I were talking about, like, where we live. So I was trying to describe what this suburb feels like and I was shown in Google Maps and all that. So that's. That's what he's alluding to. So I am very, very dramatically affected by my environment. One of the reasons my wife and I left the New York area is because it's so intense and I can't help but get pulled into it, of course. And, and it was not healthy for me and we wanted to change. We went to Portland, which is toned down, and Portland felt almost like, well, I'm, I'm kind of permanently on, you know, nine out of ten speed. And everyone else there in New York, everyone was at. And I was like, this is crazy. I'm exhausted. And in Portland, everyone was on a five or six and I was like, oh, this is, this, this is great for me. I get to, I get to go faster. Where we live now, it has a mixture. It's the Midwest and in many ways it's like nicer and toned down and not as materialistic and competitive, but there's money everywhere. [00:21:23] Speaker B: Yeah. [00:21:23] Speaker A: And when I take a walk, two blocks away is a street of just incredible houses. And I go there every day. And that gets my ambition juices going. Absolutely. [00:21:34] Speaker B: Of course. [00:21:35] Speaker A: Now the thing is, I can kind of acknowledge that it's for absolutely no, no good reason for me to go from my house to two blocks that way is pointless. There's effectively no difference. But I am still impacted by it in many ways. I need it because my default nature is lazy as hell. So I need the external poking and prodding, I think, anyway. But what you're describing in Japan seems to fit your personality. Like, it's affected your personality and your outlook and your ambition the same way you're saying, like, if you were in Sydney would be different. But I also think that's part. That's like your nature and that's why you feel so comfortable there. [00:22:16] Speaker B: Yeah, I, I don't know. I, like, I, I think I could change. I think I. If I lived in, if I, if I lived in Toronto or I lived in Vancouver or I lived near you, I could totally change my brain, I think. [00:22:28] Speaker A: I think my brain, a group of peers and you'd say, well, here's my peer group and I want to go to the top of this peer group. [00:22:33] Speaker B: That's. [00:22:34] Speaker A: That's might be part of it. [00:22:35] Speaker B: I think it's natural. I think that's what humans do. I think, I think that is inherently what humans do. I think if I took Jordan Gal and I shoved you in Thailand, in Bangkok or Chiang Mai with your family, and I set up your life all perfect and stuff, I think you're. And, and Rosie was spinning off, you know, let's say Great cash for you and your family, and you're pocketing stuff. I think you would shift. I think. I think things, things, things would. Things would shift. But I think. I think, like, where you are now, like, the life that you've got, like, you're hungry to build Rosie into a company that can then provide all these things for your family and yourself and all that. And. And you know, that intrinsic motivation that you have, you keep telling yourself, does kind of. Kind of feel fuel you. And I run into times where I'm like, I don't think I have any goals, like, at the moment. So I just work, and I don't think I have any goals right now. And I make them up. I'm like, oh, it'd be nice to hit this mri. But I'm like, I don't really care about that. Or it'd be nice to have this customer account. And then I tell my wife, and I'm like, a pretty lame goal. It's just like a. Not. Like, it's very hard for me to get hungry about these numbers. So then I default just to doing good work, and that's. That's what I do each day. [00:23:45] Speaker A: Okay. I think that's a positive approach to it. [00:23:49] Speaker B: Maybe. I don't know. Okay, well. [00:23:51] Speaker A: Right. I want to say something nice before I challenge it. [00:23:54] Speaker B: Good. You can challenge it. [00:23:56] Speaker A: Okay. How much longer? How much longer can you stay inside of those borders in that arrangement? [00:24:07] Speaker B: I find that that question's kind of like asking, how long can you go to the gym for? So I've been training since I was 15, and I kind of really don't ever miss sessions. And I love going to the gym, and I love working out and stuff. And I think when I'm 60 or 70, I will still be working out. And I kind of actually treat like Bento. Bento is kind of like, working out for me. I go in, I do my reps, I do some sales, I write some code. I do this and that. I do my reps each day. But it really could be something else. It's just Bento has the momentum behind it and provides for me and my family at the same time. Like, I think you've seen, I've tweeted, I've got, like, a little side project that I spun up called Tatami, which is kind of interesting. That's also just doing work. That's just like me. Me doing work. And that also benefits Bento in a whole bunch of different ways as well. And so, yeah, it's just I kind of wake up each day and I find being constrained to, all right, like, what's the most important thing I should do today? What motivates me? What am I hungry for? And I just kind of work on that and that helps me, I think, continue working for a long time because I'm working what I truly want to do instead of kind of burning myself out. Like I see some tweets from some founders and stuff where, you know, they're just grinding on some marketing channel trying to get that to work and all that kind of stuff. And I'm just like, if I had that attitude and I was really burning myself out trying to figure these things out, I would burn out. And I probably couldn't go much longer. [00:25:31] Speaker A: Yeah, I think it's healthy as an approach to look at it as it might be Bento, it might be a different product, might be a different business, but you are going to get up and go to work. So doing that and doing the best version of it possible. I guess what, what I have difficulty identifying with is I'm so focused on the end goal and then working backwards, it's almost the opposite approach. And I think that leads me to struggle to be as happy and satisfied on a day to day basis. Right. If I just viewed it that way, I'm just gonna go do my best work. Here's what this week looks like. This, this day looks like, I guess for me, I can't. I'm kind of living in those two levels at the same time. If I'm being honest. I live mostly in the future level. Future focused. Here's this goal, here's what's next, here's how we need to get there, and then I dip into the day to day. But I really kind of enjoy living out in the future. [00:26:34] Speaker B: Yeah. So I think like kind of on that note, the way that I think about it is my future is going to be partially dictated by what I'm working on. So if I, if I talk specifically about Bento and if I actually do want to be a little bit more forward thinking. So at the moment, Bento is a marketing and transactional esp. So people sign up, they send just like convertkit or Customer IO or you name it. Right. What we're being exploring at the moment, which I think is, is interesting, is I built Tatami, which is like a monitoring solution so you can basically pump it with all of its data and it can track all your emails and I can work out which senders are bad, which senders are good, all that kind of stuff. So It's a compliance tool. We've got a whole bunch of ESPs on it, some big ESPs using it, including us and talking with them and doing that work has been really interesting. But then we started going, okay, cool, so we use Sendgrid and we've also self host our own email servers. So we send our own emails. And that was also exploratory work we did a few years ago, I did a few years ago and it all works pretty well. So as I'm kind of like working on all these things, I'm like, wouldn't be great if I could basically offer self hosted email for everyone. What if I could disrupt the whole market and say instead of postmark, everyone's paying per email at the moment, right? And people are pretty unhappy across all of them. Currently I don't pay anything per email, it's free for me. So what if everyone could have that? So $30 sent unlimited emails, all that kind of stuff. So at the moment I'm kind of tinkering on what would like a bento cloud hosting solution look like. And I'm currently on my day to day work, I'm exploring that and I'm tinkering on that. And so long term that, that may be something that I work on where it's like I'm kind of working my way up the stack and I end up building planet scale for email. And I think that's really interesting. But I don't want to think about that far ahead. I want to be like naturally pulled into that work if that makes sense. So I'm kind of letting my work dictate the future path and I keep, I keep pulling on it and sometimes I pull down something, I'm like this sucks. I'm just going to completely dish that work and not, not try it again. But lately I've had quite a lot of wins where. Well actually just throughout my career, every time I like pull on something and I go based on my intuition, that has tended to work a lot better. And when I've been too forward focused or goal orientated, I've tended to take the L me personally. [00:29:00] Speaker A: Yeah, I think it's cool, it's just different approaches to it but there is no, there is no right approach. Absolutely for sure. And so right now, right, this is multiple years into an email product. What is going on in the email market? What is happening there? It seems to shift from time to time and there seem to be fads but email is forever, it's just going to be around forever. So where do you live in that market, in that world? [00:29:28] Speaker B: Yeah, sure. So there's a. Email is very broad and actually a lot of the moves that we've done and including what I just discussed about, like, you know, proceeding with potentially like a planet scale for email solution that we may offer in the future, a lot of that has to do with what I'm about to say. So in the marketing space, we're seeing more pushback from inbox providers. So you've got Gmail, you've got Yahoo, you've got Hotmail. The past couple of years they've kind of enforced a lot more policies for security reasons, which is, which is all pretty good. But then we're seeing a lot more like kind of compliance pushback where people are finding themselves more into spam or they're just finding a little bit of friction getting in inboxes. And a large part of that is because if you think of it from like an inbox perspective, they're just like getting a tsunami of data that they then have to store endless data from all these senders, constantly people cold emailing, spamming and sending unsolicited mail, you know, decades of subscribing to things that people don't actually, you know, want. So from that perspective, I look at like Gmail, I look at Yahoo, I look at Opmail, and I'm like, well, a lot of that's junk from their perspective, right? And so, you know, I think marketers go, oh, it's like unfair. I'm getting pushback or it's unfair this and that, but really it's just they don't want to be storing so much data because it's expensive to store all that data when it's frankly, a lot of it's kind of junk. So I think over time there'll be a lot more pushback on the marketing side of things. But ISPs are really slow to like, inbox providers are really slow to act. So let's say like a 5 to 10 year. So in saying that, I think email marketing may change over time. I think transactional email is probably going to stay. Email's still kind of like the central identity to everywhere. And we're seeing people kind of lean more into magic links and all that kind of stuff for authentication, which. [00:31:16] Speaker A: The rise of Google as a software provider is interesting. Just seeing that go from a few percentage points to over 50% for basically every product I'm familiar with. [00:31:26] Speaker B: Yeah, yeah, exactly. So, oh, are you saying in terms of like, auth. In terms of Google auth Yeah, yeah, yeah, exactly. So. And any email's still the core thing there. So. Yeah. So transactional email I think is going to stay. Email marketing I think will kind of like shift. They'll probably continue to allow good senders to send and they'll, you know, probably start just nuking bad senders, which I think is good. I mean I think that's fine. Like there's a lot of people that send junk email and I don't think they should send sent email. So that, that's okay. So yeah, in short, I think if you send email that is like wanted and expected, they're kind of like the two phrases, you'll be fine for the next couple of years. If you're not sending an email that's wanted or expected, you'll have trouble. More so than the past previous few years. [00:32:10] Speaker A: Yes. I can't help but laugh because we're in the middle of a cold email experiment. [00:32:15] Speaker B: Oh really? Yes. Who are you using for, for, for your tooling? How, how, how, how are you doing that cold email campaign? [00:32:22] Speaker A: It's actually someone from like the Bootstrap Universe product is called Mail Reef. [00:32:28] Speaker B: Mail Reef R E E F. Yep. [00:32:31] Speaker A: And they have a like done for you service. So they have an email tool and then you can also just hire them to just do it for you. And, and that's what I did. And we send pretty decent volume. It has worked. Okay. [00:32:46] Speaker B: But. [00:32:48] Speaker A: You'Ll laugh. Where we are in the experiment is in the YOLO phase before shutting it down. So the like we will spin up an AI agent for you, reply back and we'll give you the phone number. Here's 50% off for the first like whatever. Like let's just make offers and if it, you know, increases the effectiveness, great. And if not we'll probably shut it down. [00:33:12] Speaker B: Yeah, I mean you can't do that on Bento with nuclear account. But yeah, well yeah, and I think, I think sending yeah on like the, you know, still in the email market I think sending cold email is again going to change. Are you getting replies, are you getting people responding or has it kind of tanked a little bit over time? [00:33:31] Speaker A: Well it's only been maybe two months and we do, we do get positive responses and we get signups from it and we have, we have paying customers from it but we have a relatively our challenge. Right. Self serve, low priced SMB. That's not an ideal use case for cold email. The ideal use case for cold email is to get on a sales call and then close a relatively larger contract Whether that's software or service, I think that's where it makes sense. And I was still interested because I wanted to see if the newness of an AI product being directed toward people who are not quite yet in the AI universe, these SMBs that we go after. I wanted to see if that offer worked because. Because I think it's worth. Worth experimenting with that kind of thing. Anything that has the ability to scale up and is relatively easy and inexpensive to experiment with is worth an experiment. I have been completely wrong on all of my guesses. So, you know, who cares about my guesses? Let's just give it a try. So that's kind of the way I look at it. [00:34:39] Speaker B: On the cold outreach side, have you considered doing like letter drops, like old school letter drops, where you do like a flyer and then you just, you know, you get all the businesses addresses and you send them out. Have you considered doing more old school stuff like that? I know one bento customer that, that's their main marketing channel is called letter drops and they crush. [00:34:56] Speaker A: Yes, I used to do that for a living. [00:35:00] Speaker B: Oh, really? No way. Yes, absolutely. [00:35:02] Speaker A: So in the US it's called direct mail. I don't know, Letter drop might be the right though. Strong term. So in one of the first businesses I ever did, it was actually my family business. I joined my dad and my brothers for a few years and it was a direct mail business and we used to represent homeowners to challenge their property taxes and then took. Took a percentage of the savings. Is a fascinating business. But the whole thing ran on direct mail. You send out 500,000 pieces of direct mail, you know, offering your service. And people back then, I mean, it's a long time ago, they would literally like sign the contract and rip the bottom off and send it back to you. And that was your contract. So if you send out 500,000 pieces, you get 3,000 customers, you know, times, you know, basically your ARPU. It was a great business. But I love direct mail. So yes, I have thought about it and look into it now. That is relatively expensive to experiment with. [00:35:51] Speaker B: Is it expensive today? I don't know what it costs. [00:35:53] Speaker A: Like it's, you know, it's, I mean, just the postage alone is what, 30, 40 cents a pop? Unless you start doing it at scale and then it's more like metered or whatever else. But it's still tens of thousands of dollars to send any real quantity. [00:36:05] Speaker B: So where's a lot of Rosie's growth coming from now? What's the main, the main channel is. [00:36:11] Speaker A: You got cranky in the main channel is advertising on social. [00:36:14] Speaker B: Oh, cool. Yep. IG and Facebook. [00:36:17] Speaker A: Just the standard IG and Facebook. [00:36:19] Speaker B: That's right. [00:36:20] Speaker A: And that has been both surprising and like a huge relief. Huge relief. [00:36:25] Speaker B: Right. [00:36:26] Speaker A: If you think about, like, my perspective in, you know, trying to grow Rosie and managing the, you know, how much money we have in the bank, all that stuff we pivoted from rally into Rosie. So in that situation, I'm like, okay, I'm, I'm burning money and I got to get to some real revenue growth as quickly as possible. The fact that advertising worked meant I could just push, I could just spend more. Right. Not every channel is like that. Not every channel is just, well, okay, if it's working there, just spend more and it'll immediately just go up with the spend. And so I think it was a really critical aspect to getting Rosie off the ground. We basically just went, you know, zero to a million ARR in like whatever it was, eight months by just pushing. It just worked and I just spent more. And then we got to a level of revenue that really dug into the burn and all of a sudden we were in a healthy place. [00:37:22] Speaker B: Yeah, that's, that's, that's lucky. That, that's really lucky because. Yes. Pays really tricky. And is this, is this you managing the campaigns or have you found like a good contractor freelancer to help. Help with a lot of that. [00:37:34] Speaker A: So we hired an agency that worked with direct to consumer brands. And that was on purpose like a DTC one. [00:37:41] Speaker B: Like a dtc. [00:37:42] Speaker A: Yes. Yes, that's right. Because my take on Rosie was that it's B2B, but we're going after one to 10 person companies and they beh consumers. So great hypothesis, right? The analogy I use is like, I wanted straightforward direct response advertising. You know, like think about a skincare brand. I had bad skin. Then I found this product. Now I have good skin. Like, sign up here. And I basically just wanted that. I kept missing all these phone calls and I kept losing money because of it. Then I found Rosie. Now I don't miss any more phone calls. And she puts appointments directly on my calendar. Go here, sign up. So I just wanted that and I didn't know how to get that message out. So I found a, a D2C advertising agency and they were like, cool, we'll make videos and we'll just push it on. [00:38:25] Speaker B: So they do the creative. [00:38:26] Speaker A: They do. [00:38:27] Speaker B: So they did all the creative? [00:38:28] Speaker A: Yep. [00:38:28] Speaker B: Wow, that's cool. That's cool. And then are you doing kind of like the creator style, like, you know, like the selfie type content or is it more produced than that? What, what's like it after the call? [00:38:41] Speaker A: Yeah, we tried everything. Yeah. And, and we, we regularly switch up. So today was one of our best signup days in a long time because we released a bunch of creative today that was. It basically took our top performing ads and scripts and put it into like a podcast. I'm using quotes here. [00:38:59] Speaker B: Podcast, like the mic and stuff. [00:39:01] Speaker A: Two people on the mic and one. [00:39:03] Speaker B: Guy'S like, I've seen those ads. [00:39:04] Speaker A: Yes, yes. He's like, oh, I gotta tell you about this thing. My calendar's full. You know, and they're like, no way, tell me about it. I mean, whatever. We're just experimenting with different creative and like direct to consumer brands. What we experience is that the diversity of creative has an enormous impact on performance. It just coming out with new stuff. Every single time we launch a new batch of creative, it spikes up. And then what we do is we, we come like behind the videos with static ads and those just are able to deliver the message very, very straightforwardly. [00:39:40] Speaker B: Yeah. So top of final, top of funnel video, top of fun on video, clear offer, clear hook. Then they either visit the website, engage with the ad, then they kind of keep getting the statics until they. [00:39:49] Speaker A: Yes. And the statics are straight. Benefit. Benefit seven day trial. Yes, yes. You know, but even that, like we're, there's still so much to do. I mean, we still send the majority of traffic to the homepage, but it converts pretty well. And then it, and then it's a funnel optimization game. And I think, if anything, you know, I don't like to, I don't like to pretend like we have the greatest product in the world. And you know, you see all this nonsense on Twitter where you're like revolutionizing this thing and this will never be the same. Like, I hate that. But I'm okay saying we're the best product in the market for self serve, for voice AI. And I think that is what allowed the advertising to work because you can just spend money showing to total strangers and they will come into the funnel and pop out of it 15 minutes later with a working voice AI product that they can send their phone calls to. So that, that was the actual challenge in turning the advertising channel into growth. [00:40:46] Speaker B: Gotcha. And then you also have like an activation challenge. Right. Because people have to start forwarding their, their phone calls to you. Right. And then, and then have you resolved a lot of the activation stuff as well? Like because to Be able to grow and scale that paid channel. Yeah. Because you've got all these different like non technical users and stuff then kind of coming at scale. You then have to make sure that forwarding is seamless. And have you been able to, to, to figure that out? [00:41:12] Speaker A: Well you, you, you kind of nailed it. It's exactly our problem. [00:41:16] Speaker B: Right. [00:41:16] Speaker A: Non technical user then we can do a good enough job of getting them through the onboarding so that they have like we work pretty hard and, and have redone the onboarding flow multiple times but it gets people to a place where they get a phone number and then they can call the number and, and that's half of the activation. That's almost like the emotional activation like the fact that I call it and it answers and Rosie is like hi, this is Jesse's Body shop, how can I help you? Right so that, that's the emotional like oh my God, this thing works and then from there to the actual activation of it picking up the phone. Cause you have to forward your phone number to it. That's the biggest challenge in the business and that's the single biggest factor to conversion. [00:42:06] Speaker B: Yeah, yeah. I mean Bento has the same problem. So I'm just kind of, it's always interesting to hear people. [00:42:12] Speaker A: Yeah. Can you describe what's your challenge here? Actually hitting sense. [00:42:16] Speaker B: I got a lot of challenges. No, I got a lot of challenges. [00:42:19] Speaker A: Well keep email. Honestly. Honestly email sounds so challenging. [00:42:23] Speaker B: There is a lot of. Yeah, I don't even know where I want to start. Like a lot of people kind of come through and they come from various sources. Right. And they come from various levels of technical knowledge. To actually send email, you know you need to add DNS records and stuff like that. That's really scary for everyone and I've looked at ways of making that smoother and all that but then I've kind of come to the conclusion that I kind of, I don't necessarily want to be serving people that are super non technical high support and so we kind of have this niche where we're kind of somewhere between kit and customer IO. So for more technical people, even like technical creators and stuff we've got like a lot of, a lot of the more, you know we start getting a lot more kind of kit customers that kind of grow out of kit. The automations can't do what they want. They don't want more control flexibility, they want more control. They're running multiple websites, all that kind of stuff or you know, they want to start doing stuff with webhooks. Or Nadan or all that kind of stuff. Bento is a great fit for that. And so I've just kind of more focused my energy on making sure that like, yeah, I'm just serving those people better. And a lot of our focus in the past couple of years has, you know, with Zach, who lives in Dazaifu, he's spun up a whole bunch of different Dev libraries and SDKs and stuff, which has attracted a lot more developers. So, you know, we've got Go developers and Python developers and PHP and Laravel and more Rails developers. Like they've all come from us launching those SDKs and making it better. So our customer pie has really shifted. So it's kind of more technical businesses. You know, you think about like a WordPress info website that's selling a whole bunch of products. It's got a lot going on, a lot of lead forms and all that. And then you've got your developers and SaaS businesses and all that kind of stuff. So yeah, and then those ones, they've got less friction. [00:44:11] Speaker A: They have less friction because they know what they're doing. [00:44:13] Speaker B: Yeah, they know what they're doing. [00:44:14] Speaker A: So it's not. [00:44:15] Speaker B: The engineer or developer or founder is setting up the DNS records. And so that's how I tackle. I basically tackled, yeah. Solving the onboarding friction with basically changing who I serve. And I think that was a little bit easier. [00:44:29] Speaker A: It's positioning. Right. And of course, yeah, right. The email market is big and therefore you can pick a spot as long as you do a good job for them. So it's almost like they know what they're getting and you know what they're getting. [00:44:42] Speaker B: Exactly. [00:44:42] Speaker A: Right. They're not asking you how do they do DNS, they're asking you much more in depth questions and the. Their decision on whether or not to go with bento is going to be based on if they can accomplish what they want with your system. [00:44:54] Speaker B: Yeah, yeah. And the answer is probably yes. And it's a lot easier to have that conversation. And then, and then advertising has been a lot like easier for me. So like I actually, I sponsor podcasts and stuff. I actually really enjoy that. I sponsor creators and like the mostly technical. I like sponsor them, which you listen to probably. [00:45:09] Speaker A: I had a good laugh today. I was listening to the mostly technical podcast and they were doing the read. Have you listened to it by chance? [00:45:16] Speaker B: Yeah. Not today's one. Not today's one. Not today's one. [00:45:20] Speaker A: So they go to do the bento read. I think Aaron goes, whatever is on my Website. Because that's what you told them. [00:45:30] Speaker B: That's what I put on, yes. Yeah. [00:45:32] Speaker A: So he. Then he goes to your website and he goes, bento is the solution for. Right. Basically, what's on your site. So that I feel like that fits, like, your whole vibe and what the business vibe is. [00:45:44] Speaker B: Yeah, but also there's, you know, we've used the word a few times. There's a little bit of arbitrage there because the media. Mostly technical. It's like a niche podcast. And I love those two guys and all that, but I wouldn't keep giving them money if it didn't work. And so it does work. And the reason it works is it's got a whole bunch of people that are a great match for Bento. A lot of those people also work in companies that some of them have decent list sizes and decent customer bases and all that, because, you know, it's just technical people watching and so sponsoring people and companies, like, mostly technical. There's just, like, a little bit of arbitrage there. And in the email space, there's not really too many places. I can't do AdWords. I get PRI. I got people bidding on all my branded terms nonstop. You know, I can't SEO. I don't even. I was an SEO before, and I don't do SEO because, like, I can't compete against HubSpot. I just can't. Yeah, those guys are the goats. So mailchimp, I can't compete against. In their activecampaignweb, there's, like, thousands of people to compete against. [00:46:41] Speaker A: Right? That's right. [00:46:42] Speaker B: And so if my goal is to not die and have this business continue living, then I have to kind of work out these pockets of customers where there is a little bit of arbitrage and they're not gonna churn, and I can support and serve them well. And that's kind of how I compound, and that's how this business compounds. [00:46:59] Speaker A: Okay. [00:46:59] Speaker B: Yeah. [00:47:00] Speaker A: Very interesting. The. You'll like this. When I talk to investors, the analogy that I make for Rosie is in the email space, and I say, if email gets invented, I'm not building Klaviyo. I'm building Constant Contact or mailchimp. And that is my reasoning and the analogy that I used to explain my reasoning around Rosie being very, very horizontal and not vertically focused in any way on an industry. And it's because, look, this thing just got invented, and there are about to be a million small businesses onboarding into one of these products. And so that. That positioning is, you know, it's very, I think it's logical for me, but very, very much the opposite of what your experience in the actual email field. Not the analogy of it. [00:47:49] Speaker B: That's an amazing analogy. I couldn't agree more. Yeah, no, I couldn't agree more. Rosie is to mailchimp. Like mailchimp's a great example of this mailchimp. You can't talk to anyone. Their support's slow. They publicly say they don't want to talk to anyone. I mean that's in like the Intuit buyout docs, right? Like they're celebrating. No, everything's self serve. You know, we've got all this AI to make sure we block all the spammers and all that. Like they're very, yeah. Adamant about it. And what's the guy's name? What's the. [00:48:15] Speaker A: Ben. [00:48:15] Speaker B: Ben. Ben, yeah, yeah. Like, like, you know, Ben's a phenomenal founder, but that's what they've always been focused on. They want to be self serve first and then that's how they find their way into, you know, being integrated into WooCommerce when you sign up. That's how they find their way into all these things. And that's an entry point. That's how their business runs that, that's how their business runs. Right. Like mailchimp everywhere. [00:48:34] Speaker A: Which, yeah, mailchimp is okay with someone graduating out, going to bento. [00:48:39] Speaker B: They don't care. [00:48:40] Speaker A: That's right. That's part of the, their fact that's factored in. And I guess that's, you know, I think very much the same way where I know for sure. I mean it's already happened. It's only been, it's a year old, but people graduate out into more verticalized solutions that go deeper into their industry and have the integrations and the super special features. And it has really helped me to look at the email field and remind myself that it's okay for us to just stay exactly where we are and not be in a rush to build every feature and be okay with watching people just leave because it's right for them to leave. Right as it matures, it'll change. [00:49:19] Speaker B: If you try to be klaviyo right then it's like Rosie's gonna have a workflow builder and like all these kind of like crazy setups. You can't, you can't and because the minute they then that traffic which you have now found that's working like comes in and then they see like a crazy setup and a lot of config, they're gonna, you know, hands up and leave immediately. And that happens to Bento every day in like, the cancellations. Overwhelmed. Too complex and all those. I don't really care. Like, I'm happy they're leaving because they're not a good fit. And on a good. Yes, yes. [00:49:48] Speaker A: I, I, I, I still find inspiration in Jason Freed and his work and the comfort he has in just staying right where they are. You know, when you described your, the joy you get from the habit of work, like, like exercise, that's what I think of as an example on the web of someone who just wants to do good work and is not in a rush to hit some goal or sell the company or do something else. [00:50:16] Speaker B: What are you doing day to day? What is your day to day? [00:50:19] Speaker A: It changes. So I, let's, let's think about a day. I like a good day. [00:50:24] Speaker B: Yeah, yeah, yeah, yeah. Of course. [00:50:26] Speaker A: I can tell you what a day I don't like is. Yesterday. Yesterday was Columbus Day here. It's quiet. I had a totally open day with like, no calls and I don't do well in that environment and I procrastinate and I don't get that much done. And at the end of the day, I'm like, I had a whole day and I barely got anything done. And now I'm a little miserable and upset with myself and I want to do better tomorrow. The opposite version of that is calls. And I'm clearly extroverted and because calls make me happy and excited and it gets all of my energy going and I can do more work in between calls than I can if I had a whole afternoon with no calls. And that's just weird. But that, whatever, that's me. [00:51:03] Speaker B: I'm, I'm smiling. I need calls to help. [00:51:06] Speaker A: Yeah. So on, on a day to day basis, I like to have a mix between internal and external conversations and I like to take a walk because that is usually where the good ideas come from. And then I come back to my desk and maybe execute on one or two of those ideas. So it ranges from in the morning. Well, this morning I spoke to an advertising agency because I'm, I want to see what else is out there. And I got introduced to these guys in, in, in London. So I spoke with them and wanted to hear what their approach is and how they would approach Rosie to kind of pull some of those ideas in and also have like a, a bank of options if I wanted to switch. Then we did standup, then I had a leadership call, and then I had lunch and I had A long walk. And I came back with an idea on who I should reach out to to set up an integration. And then I kind of tried to track them down. So that's, you know, that's kind of, that, that's a happy day for me because I, I got the juices flowing. I talked to the outside world. I improve things internally. We have, you know, a relationship challenge happening inside of the company right now that I want to improve. And so I had a hard conversation today with someone on the team. I was dreading that all weekend. And then, and then I did that and I felt better about it. So I guess it's this kind of mixture of like interpersonal conversations, ideas, a little bit of outreach. [00:52:31] Speaker B: Yeah, but you are very much in that like operating CEO role, I think. Right? And yeah, you're managing people, you're managing emotions. And I think maybe your day to day and how much you like your job kind of is dictated by, I guess, how people are feeling. Because I found that a lot in like the agency. A part of why, like I've strictly not hired, maybe to my detriment at times, is like, I just, I didn't really like having so many like, connections on me. Like, I felt like every person I hired, it's like, it's like a connection. And, and I think I, when I got rid of that agency, I kind of like severed a lot of those. And I've. And I've been hesitant to kind of add more on because, yeah, like when you're operating and you're managing and you've got humans and stuff, I think it is, it's natural to have ups and downs and get burnt out and stuff. And I, I'm trying to avoid that this, this time around, but, but then that comes at a cost because it means I got to do all the work. So. So this is just trade off. Right. So it's like, well, if other people are doing the work, then I now have like this emotional cost and I have to manage that. And, and I'm making a decision and a constraint not to do that. But then sometimes I wonder, maybe I should, you know? You know what I mean? Does that make sense? Absolutely. [00:53:44] Speaker A: Well, well, right. I can't help, but you and I are mirror opposites in many ways on this. [00:53:51] Speaker B: Yeah. [00:53:51] Speaker A: Because the people and the connections is what I'm really good at. And the work you got, the work I am not good at, honestly. And so I guess both of us have arranged our businesses to match our preferences and our strengths. So in many ways I Do the least amount of work in the company, no joke. And that's kind of on purpose. And, and it's, it is, it is an interesting element to the company's DNA because everyone knows it, I know it and they know it and I know that they know it, that, that I do the least, that I do the least amount of work. But as long as I prove myself invaluable in certain ways, it's almost like it stays in equilibrium. [00:54:44] Speaker B: Well, the work wouldn't exist without you. So I mean, like, and without you pushing and managing and steering and the like. Of course, you know, if you didn't hire the agency, you wouldn't have any revenue coming in, right? Like, yes, all that kind of stuff. If you reach out to the guy this afternoon, you won't have this integration that comes up that brings in some more customers, that keeps everyone employed. So. Of course, of course. Right, like you are very valuable. But. [00:55:06] Speaker A: Yes, but it's, it's a, it's a. So it's one way of working. Right. It's, it's my version of, of pushing things forward and adding value. And I'm probably, you know, shortchaining myself a little bit, but. And might be exaggerating, but, but that's the truth. Now I have to ask you though, you. You're a bit of an extremist. [00:55:25] Speaker B: A little bit. [00:55:26] Speaker A: You don't have any, any other full time employees. I, I'm sure there's a lot of work. Is there any part of the work that you think, you know what, someone would actually be better off doing this? Whether it's because you don't enjoy doing it or because you're not the best, you know, X engineer in the world or you don't enjoy a certain part of it. [00:55:47] Speaker B: Yeah, I mean, I mean, I mean people, people are much better than me a lot of things. Right. I had someone on Twitter, I don't know if you saw it, but someone, someone dragged me on my marketing stuff the other day. I won't mention their name, but they did. I'll see them in Bangkok in a couple of days. But you know, like, it's tricky because I hired last year, I had some people, some external contractors to help me on some development stuff. Stuff, specifically upgrading a whole bunch of our rail stuff to like the latest versions and catching all of that kind of stuff. And it was a really good engagement. Now I tend to do that. I find people that are experts at the field they're in, bring them in like a mercenary. They tackle something for me, for with me for a short period of time and then, you know, we become friends and I may bring them in later. Like I'm thinking about that for some postgres stuff. So sometimes I hire people just to talk and think about things and then I'm usually the one to actually execute it. So I'm not like, I'm not going to work with anyone. I just try and work with people that are experts and just bring them in just for a little bit of time to help me learn a lot of the time, right? Like, if I've got an elastic search question, I'll bring in an elastic consultant to help me understand how it works and I'll implement it myself. Now things have become really different with Cursor and all of that. And specifically things changed a lot for me when GPT5 and actually this year before when like OPUS was released, you know, like when the OPUS model kind of came out, like the Claude stuff. And I started doing a lot more AI work and I started using cursor background agents and I found that like, with Opus, you know, things were pretty good. But I'm finding actually in like the last six months with just cursor and background agents and GPT5 in particular, it's like, it's really good. Like, it's, it's really good and I'm, I'm using it a lot more and I'm working with AI a lot more. And you know, I spend thousands of dollars a month on, on contractors for, for dev and for, for, for $2. Like I, I even, I, even as a test, just because I just want to see what it was like, I, I basically chucked the same tickets at, at the AI that I was doing kind of before. And it's like, you know, we're talking, you know, 50 cents a dollar to get that same work done and it's done in 10 minutes. That's crazy. It's good now, it's good now. So it's not bad. It's like, it's good, it's good code. And if our code base is really mature, so it's leveraging a lot of what's already been written. It's writing in the same styles, all that kind of stuff. So I'm not doing anything crazy. So in that regard, there's a lot of development stuff, which is the hardest, which technology is just improving at such like a rapid rate that you can, you can go really far as an engineer of one, you need people less. [00:58:25] Speaker A: Than, less now than you did a year ago or two. Years ago or three. [00:58:28] Speaker B: Yeah. And then a lot of the challenges become on infrastructure and a lot of the infrastructure, you know, you can work with planet scale or you can just buy more machines or you can buy more ramp. You can just keep. If you have revenue, you can buy more. If I run into an elastic cluster issue, I'll buy a big air force until I fix the problem and then I solve and then I can scale back down. Right. [00:58:49] Speaker A: So what about the softer stuff though? A customer support. Sales. [00:58:53] Speaker B: Yeah. So our sale. Our sales. Our sales is a little bit different, so people can book demos with me whenever they want. I've moved a little bit of focus off that recently. I've like moved the CTA a little bit off just to see if it has any impact on revenue and it hasn't really seemed to. But yeah, I talk to people, I'll do walkthrough calls if people need help or whatever. And usually it's like a hundred percent they're locked in after that call. So once I talk to someone, like they're not going to turn, they'll, they'll sign in, they'll continue. So for me it's like, yeah, that's going to. Yeah. But if they're going to be a customer for, what is it, let's say a few years, that's, you know, hundreds of dollars of revenue. So it's worth my time actually doing one call. Yeah, sure. So that's the demo side and then the support side. I push everyone to Discord and Bento runs on Bento Chat, which is our support service. And I built using AI, like an AI agent offering. So Bento Chat, the first tier is answered through our AI. So someone emails support or emails our approval emails, whatever. AI responds and then it escalates after it's got the information that it wants and people really like that. So our support loads dropped. If I notice like an, an issue from support, I try and fix it with code instead of docs. So I always default to trying to fix issues with code instead of docs. That's like a thing that I, I kind of believe that helps. Yeah. And then everything else goes to discord and then other customers answer customers for me and that's great. [01:00:19] Speaker A: So okay, you, you are, you are operating a. It's almost like you were ahead of your time a few years ago and now it's like now it's perfectly fits the environment. Right. Where all the leverage is now really maturing in all these different areas. The development, the, the infrastructure, the support. Yeah, it's it is very strange to see a company grow and just not need more people. But that's kind of the era that we're in now. [01:00:52] Speaker B: And you're totally right. A year ago I, more than a year ago, like let's say two years ago or whatever, I, I, I felt this was happening. Like I, I felt this was happening. But things, you know, hallucinations and all that were a lot more prominent and it was harder to like, you know, get the models in a headlock to do what you wanted. But, but now, now you can like even like on the compliance side, it's like I know Kit has a compliance, a full time compliance team. I like every ESP has a full time compliance team and they usually have a support person who's like, and I talk to these people with tatami, they're like just glued to the thing trying to work out who's spamming or not. With Bento, I've just got like an AI agent. It's just like constantly running on templates and randomly sampling emails just to make sure people aren't doing things naughty. Right. And, and we catch stuff, we catch stuff all the time and it's, it's been really, really good. So yeah, yeah. I, I think we're finally in this era where if you're an engineer and you don't mind talking to people so they're like the two caveats and you build something in a market that has demand and is in like a clear category. Right. I think a single person can make like a 10 million plus dollar business a year. And that's totally feasible, totally feasible now. Whereas before it was like, yeah, maybe a freak would do it. [01:02:00] Speaker A: It was a freak. Yeah, it was a freak. [01:02:01] Speaker B: Yeah. But, but now, now I think there is the opportunity for everyone to be that freak. It's still extremely hard. I think it's still very, very hard. But I think it's possible now for a lot more people. [01:02:11] Speaker A: Right? It's, it's almost like the, the, the dream of software and you're building it once and sell it a million times is, is actually closer to real than it used to be. Where conceptually that's true. In reality it barely exists. Barely exists. [01:02:26] Speaker B: Yeah. [01:02:27] Speaker A: How many, how many plenty of fish stories are there really? You know, a handful. We have fun with LMS because people, people try to use our service for nefarious things, right? They try to, they'll make a million call, they'll send text messages to trying to fool senior citizens into giving their tax information. Like all the crazy the worst possible stuff. And of course they want a Rosie agent to pick up the phone and get the credit card info or the bank info or whatever else. So we have LLMs running across every conversation. It's very useful. [01:03:01] Speaker B: That would have been a full time person scanning logs. Right. Like a few years ago. Right. We're trying to work that out. [01:03:07] Speaker A: Six people full time. You inspire me. [01:03:10] Speaker B: Number one, Jordan. Do you find pressure now to hire or do you find pressure now to work out how not to hire? Because you know, like the Jason Frieden and DHH thing, which is like you should only hire when it really hurts. And I'm just finding things. You can find band AIDS, which are LLMs now. So it's like things hurt a lot less now than they used to. If I run into like a production issue on like whatever, often when that error comes up, an LLM has already like tried to fix that bug or like I'll be at the gym, a bug will come up, I'll reply in my like honey badger thing type cursor fix. And by the time I come home from the gym, a fix is like ready to be shipped and deployed. [01:03:50] Speaker A: So it's like, yeah, that's a trip. No, we. [01:03:53] Speaker B: Do you think you can go further? [01:03:54] Speaker A: Absolutely, absolutely. And, and, and we said it pretty early on and we started Rosie with six and we still have six. We do have a full time support person. So seven. If I'm gonna, if I'm gonna be accurate, the core team is six, but she's part of the core team now. So it's seven people. And the, the, the switch, the, the big change is that the leverage now is not in hiring more developers. It's in hiring in go to market. So at rally, the team was weighed much, much more toward developers because it was a very complex payment product with a vault and like. So the leverage was crazy business. The leverage was let's hire another backend engineer. Now I've told the team we're not hiring any more engineers. We're good. Settle in. Look around you. Everything you need, you already have. We can get this thing to 10 million arrows with exactly what we have right now. And the leverage will actually come from hiring a salesperson that can get us into larger organizations with, you know, a thousand unit franchises and that kind of thing. [01:05:00] Speaker B: So it's, it's flipped and they're all comfortable with that. All those, all your engineers on your team are like, yes, wait, I got Cursor or I got Claude, I got whatever, I'm good to go or Any pushback? [01:05:09] Speaker A: It's not pushback. It's just like clarification. [01:05:13] Speaker B: Right. [01:05:13] Speaker A: If that's what you want, Jordan, just keep the expectations in line. Don't expect us to put out as many features as we would if we had more. And even that we both challenge ourselves on. Because right now, with three engineers, we are moving faster than we did when we had 15. And everyone enjoys it more and it's easier, it's more straightforward, and the organization's completely flat and everyone's like, all right, you take this ticket, I take this ticket and kind of just move on. I think it's like the perfect startup size. [01:05:47] Speaker B: 100%. Yeah. Six is a great team size. Six is a great team size. [01:05:51] Speaker A: It is a product manager, backend, front end to backend, front end product manager. And then two people on go to market, myself and one person on, like, customer success and sales and biz dev. That's it. It's like a little, tiny little org. Everyone has their little battle station. There's almost no overlap at all. And you can get a lot done. [01:06:14] Speaker B: Yeah, you can get a lot, a lot done. And you can go, you can just go, like, so much further. But I think it's also really empowering to know that, yeah, you can go, you know, you can 10x your size on that same kind of, like, team. And there are, there are ways to help with that that don't mean adding more humans, more connections to you that'll kind of make you a little bit more lethargic, I think, over time. [01:06:32] Speaker A: Yeah, yeah. And I think a lot of, like, peers that I talk to or that are similar boat. There's definitely the path that we see on Twitter, which is raise an enormous amount of money and buy GPUs and, you know, boast about raising a hundred million dollars in less than two years kind of thing. But a lot of startups are looking at it and saying, I don't want to raise any more money. Like, why? Why would I rush to the next round when we're six people, we have plenty of money in the bank, we can get profitable. Like, why would we rush to raise more money? And a lot of VCs don't know what to do with that because their business model is like, wait, hold on a second. I thought we were going to push this further and harder and faster. And so as the team, you almost have to show the investors, like, well, there isn't a direct connection. Taking an extra 10 million bucks does not mean more growth. It might actually mess things up. So there's definitely a push and pull between the revenue growth and how much money you're raising and how your investors think about it, how the team thinks about it. But internally, on a day to day basis, it's fun, man. Six people. You, you know, we went to San Francisco a few months ago. It's easy. Six flights, you know, a couple hotel rooms, a couple of dinners and, and that it feels so much more manageable and fun. [01:07:48] Speaker B: Yeah, that's nice. Where can I keep asking questions? I absolutely can keep talking. I mean, look, it's your call to keep going. [01:07:56] Speaker A: It's 9:15pM I grabbed the beer. You know, I'm good. I, I know you are in no rush because you got no one to answer to. Yeah, go for it. [01:08:05] Speaker B: Yeah. And it's a beautiful day, got the sun and it's nice talking to you on like, the investor side. How, how, how do you manage investor expectations now in terms of like, where Rosie is? Because this is something that, like, I haven't really explored, even with Bento, where it's like, well, what if I decide to raise money? Like, what if I decide to go the next step? What outcome do your investors want to see other than like, you know, the billion dollar unicorn? What's like, their realistic expectations of Rosie? And how do you manage the investor side? And has that been, I don't know, difficult over time? Like, what's it like having investors on the board? [01:08:43] Speaker A: It has not been difficult, it has been great. So, and I don't know how common that is. [01:08:49] Speaker B: I think it's uncommon. [01:08:51] Speaker A: I don't know what to tell you. You know, I think it's a combination of we have great investors and they', supportive, so maybe they think differently than what they say. But when I talk to them and all of my interactions, it is just positive and helpful and, you know, enthusiastic, motivational, supportive. It's kind of been good. There have been a few moments of difficulty. And then I think the, you know, my age and maturity and experience has, have kind of helped me manage that properly. Like when we pivoted from rally to Rosie, I did not ask permission. I just told them this is what we're going to do. And I explained my reasoning and, and, and you know, it was kind of like, this is, this is not, I'm not, I'm not a kid. I'm not just like doing this on a whim because it's the cool thing to do. I wrote out my reasoning and I explained why. And this wasn't sudden. Right. It's investor Updates every month of seeing, just trying really hard, Trying really hard. Trying really hard. Imagine doing that for two, three years. You start to have some respect for the other person. And if they come back to you and say, I think we're actually done, this isn't working, we're going to go a different way, you know, try hard at this. Right? What are you going to, you going to be mad at them? You know, so you use the word in your question. That I think is the key to answering your question. You said realistic expectations. There are no realistic expectations. Realistic is not part of the equation. It's not anyone's fault. It's the nature of their business. The nature of their business is to invest with the potential of gigantic returns. Anything other than gigantic return really doesn't matter. Math, math. Mathematically it doesn't matter. [01:10:37] Speaker B: And they've already factored that in, right? [01:10:39] Speaker A: They've already factored in there. They gave money to rally because we were building a shopify like checkout for the headless E commerce ecosystem and we had a token model behind it that we were going to give out tokens, crypto tokens based on the amount of revenue processed through the checkout so that the merchants would own the checkout itself. You know, that description is insane. And investors were like, yes, you said it. Yes, that explanation is insane and you probably won't succeed. But if you do, that might be like a, you know, defining company in E commerce space. And so that's why they, that's why they put money in. And if it didn't work out, they're basically like, okay, you know, didn't work out. That's, that's, that, that happens. The truth is that that happens nine times out of 10, maybe 95 times out of a hundred. So they don't have realistic expectations. Their expectations are that you have made a bargain together. You have made a deal. We will give you an enormous amount of money. You can do whatever you want with that money. We're not really gonna tell you what to do. All we want to know is that you're trying to make it an astronomical hit. [01:11:48] Speaker B: That's it. [01:11:49] Speaker A: That's the deal. And so as long as you know that that's the deal going in, then everyone's kind of on the same page. [01:11:56] Speaker B: Yeah, that, that, that, that's, that's kind of, that's kind of cool. And then if, if with Rosie, like, if it gets to, let's say 10 mil, ARR, or whatever, right? Where's like the, the exit point? Like where, where would you start exploring, leaving that. Like, if you're gunning for the 10 mil, then I have no idea what that would sell for. But, like, if you hit the 10 mil, or do you have to hit the 100 mil, like, where's the expectation of where you need to hit? [01:12:20] Speaker A: Yes. So. So that's the realism, the realistic that comes in when you've been knocked off of the ideal path. [01:12:30] Speaker B: Right. [01:12:31] Speaker A: And that basically happens as if you don't have big growth right away. You are almost certainly going to be off the path and not raising, you know, an A and a B and a C and a D right after one another. [01:12:44] Speaker B: Yes. Yeah. Yeah. [01:12:45] Speaker A: And so that's where the realism comes in. That's where we're like, okay, you know, what. What are you going to do with this thing? And in our situation, because we pivoted, we went from an assumption of zero to all of a sudden, hey, look at these guys. They pivoted, and this thing's actually working. It might not be a zero. Like, it's almost like we got nothing to lose. All right, cool. Let's see what you guys can make of this. So when you think about an exit, look, if I came to them and I said, guys, we got an offer on the company for 50 million bucks, they would say, if that's what you want to do, we're not going to stop you. We'll support you. We want you to do what you want in your career. And if you tell us that's what you want to do, we're not going to stand in the way. We'll be with you, and we'll wish you luck. And maybe you have another idea, you come back to us for. For more money. But that's. That's very different from, oh, my God, $50 million. Unbelievable. You're the man. Like, it is not that at all. [01:13:43] Speaker B: And that for sure. For sure. [01:13:45] Speaker A: And that's not bound. [01:13:48] Speaker B: It's all good in the 50. Yeah. Sorry to be nosy, but in, like, the 50 mil, would you have, like, a good. A good outcome from that? Like. Like, where. Where do the great. Where's there, like, a great outcome for the investor and then, like, a great outcome for you? Where's. How does that kind of play out? [01:14:03] Speaker A: Okay, so this. I think this is worth getting into because I never really came across this stuff before, and now that I live it, you kind of understand more of. [01:14:12] Speaker B: The sorry to be nosy, by the way. No, no. Why? [01:14:15] Speaker A: I think it's good. I enjoy talking about it because it's really Hard to get this information. So here's what it looks like. You have a preference stack. Your preference stack is almost always, let's say usually the amount of money that you raised. Let's just say you raised 10 million bucks. In those documents, you likely have a 1x liquidation preference, meaning they get one time, their money before you get your money. So they're the preferred investors with preferred shares and they get paid back first and then the rest of the money goes to common stock. So there is an, there is an in between space. Let's just say you raised 10 million bucks and you sold for $9 million. All $9 million would go to the preferred. Nothing goes to common. [01:15:01] Speaker B: Okay, gotcha, gotcha, gotcha. [01:15:02] Speaker A: Now let's say you sold for 15 million bucks. 10 million would go to preferred, 5 million would go to common. And there's a space in between the preference stack, how much money you raised, and the valuation of your last round. And so let's just say you raised 10 million bucks and you were valued at $50 million. If you sold for $12 million, the preferreds would get 10 million. If you sold for $45 million, the preferreds would get ten million. As long as they're not participating preferred, they get paid back first and then the rest goes to common, which is. [01:15:36] Speaker B: Basically the team 10% that everyone has. [01:15:38] Speaker A: Yeah, that's right. And then as soon as you get over the last round's valuation, you start to creep into territory where pro rata. So you're not worried about the, the preference stack. If you sold for $70 million, you wouldn't worry about the preference stack. It's above your last round's valuation and therefore it's just pro rata who owns what percentage of what. And 70 million gets divided by, by that. So there's this, there's this, you know, this funny dynamic around. If you sold for 40 and you raised 10, the team would make $30 million. So that in that in between spot, you're kind of like, it's, it's very ambiguous because the preferreds don't make any more money if you sell for 12 million. Or if you sold for 40, they just get their 10 million back. [01:16:24] Speaker B: Yeah. So it's. So then you're kind of in this like, you know, it's funny because like in a bootstrap company, you're like, you're gunning to pay your weight, like your salary and food and rent and stuff. Right. And then in this kind of like funded model, you're gunning to pay the preference Stack and then once you, and then you try and blast past that evaluation after. Right. Because that's, that's okay. Cool. That, that makes, that makes a lot of sense because I, I, I do think about it with Bento. [01:16:48] Speaker A: It's very restrictive and, and I wouldn't recommend it to someone who has a business up and running and off the ground. Especially like beyond. Call it a million or so in ar. [01:16:58] Speaker B: Sure. [01:16:58] Speaker A: Yeah, yeah. It's really tough to make work unless you structure it differently. Look, if you're, if you're at zero and you have an idea for a product and you go out and raise a pre seed, I mean how amazing is that that someone just gives you money, you start to pay yourself a salary and you. [01:17:13] Speaker B: Phenomenal. [01:17:14] Speaker A: It's phenomenal. And, and if later on you don't get as big of a return. Yes. And if you don't get as big of a return, like that's the trade off. They paid your salary for years. So when I think about that, I'm like, oh yeah, it's, look, it is, it is a, it's one of the key reasons that innovation is what it is in this economy in America and beyond. Because this risk capital allows people to do that. It's, it's good for everybody all the way up and down the stack. But if you are bootstrapped and you own everything and you're at a million ARR. And someone comes along and wants to buy your company for 10 million bucks, you're going to make $10 million. That's, you know, that's life changing. If you raised money, it's not life changing. And that's kind of what you, you know, you have to know going in now there are still ways to structure. So I think finance and structure is ignored in the bootstrap world too much. There is so much leverage and advantage in finance and structure. So for example, let's say I'm running a million dollar a year bootstrap company and I'm considering raising money that might actually be an opportunity to sell some of your stock to the preferreds and take four or five million dollars off the table directly and de risk your taking on outside investors that then all of a sudden have a say over when you sell and when you don't sell and everything else. [01:18:37] Speaker B: That makes a lot of sense. [01:18:39] Speaker A: Right. So there's, there's, there's a lot to do there and there are some people who are exceptional at structuring things and, and they can, they can help you or, or they can wreck you but if you, if you kind of work with good people, they. There's a lot of magic to be done in structuring. [01:18:58] Speaker B: Wow, that's fascinating. Yeah, that's, that's, that's fascinating. If I ever, If I ever decide, let's say for bento, cloud, planet scale, email, if I decide to race for that, I'll book a call with you. You can tell me. [01:19:12] Speaker A: Separate company, different ownership. Yeah, all that stuff. [01:19:15] Speaker B: I've also noticed there have been a lot of founders also going to. For finance and stuff like, especially founders that kind of like figure out, you know, basically taking loans out to. If their ads are working and they try and scale up that way. And I've noticed a few founders going down that path instead of selling equity, actually taking out a loan to scale. But yeah, there's a lot of different paths. But at the moment I just want to kind of stay, stay, stay, stay. As is. It seems to be working. [01:19:41] Speaker A: I. I have to say, you got a good thing going, you know, be. Be hesitant to mess with it. Oh, well, my man, I guess we should call it, right? It's been an hour. It's been an hour and a half. It's. [01:19:54] Speaker B: I'm hungry. [01:19:55] Speaker A: Yeah, I think I might go to bed soon anyway. [01:19:58] Speaker B: Nice. It was really good catching up, man. So nice. Probably chat more. It was really, really fun. And knowing that lore at the start, I'm still thinking, I'm still thinking about it. It's crazy to know that, you know, your future co founder was in the room with you as I was like, talking to you about Aussie supplements or whatever. [01:20:14] Speaker A: Yes, it was in Santa Monica, on a rooftop overlooking the beach, outdoors. I can remember it perfectly. And from all the way back in a dingy warehouse. [01:20:25] Speaker B: I was in a dingy warehouse, dust everywhere, protein powder behind me. [01:20:31] Speaker A: Not as glamorous, but hey, well, all the way from back then, all the way to today. [01:20:36] Speaker B: It's great to see you. [01:20:37] Speaker A: Thank you. [01:20:37] Speaker B: Yeah, you too, man. You too. [01:20:42] Speaker A: It.