John Nunemaker
Appearances
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And it was the first and only time in my life. I think I've had imposter syndrome where I was like, I don't think I can actually help you. But I was like, let's try it, you know? And between the two of us, we were able to help get it away as I brought on some other friends who are much smarter than me. That was really my value in that.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And so when I left, yeah, it was millions of requests a minute in Rails, all in Rails, and just basically wrote Memcache for like two years, a year and a half or so. And so we helped him launch on Facebook and all that kind of stuff as well. That was ordered list days before we got acquired by GitHub. Before you were acquired. Yep.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yep. Just like SaaS apps. And it is like my mom still, she still plays on it. I haven't, I kind of dropped games, but yeah. I dropped off as well, yeah. I think there's still a lot of activity. So I don't even know who owns it anymore, if it's still Zynga or not. Because they bought them at some point.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
They had all kinds of stuff that were all with friends. Yeah, it was smart. Right.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And I, I think that happens with everything. It happens with SAS apps, like anything that, you know, has stickiness is going to have that same kind of like, I guess like tail, a long tail of like, where it's just going to go like that for quite a while. I mean, just again, just since fireside, I think I've had three or four or five people, uh,
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
come up to me we're kind of in a similar boat and it's really fascinating to me because on one hand it's like the first i remember the first time i talked about it with anybody they're like dude that's that's a lot of money like what if it goes to zero and i'm like they don't go to zero they just don't like think about all these apps on the internet actually i talked to adam i forgot about that we we talked and he was like well what if it goes to zero you said that adam he said that
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Oh, close to that. I think I did say that. Yeah, that's something he would say. Yeah, go to zero. He'd say that. It was close to that. It maybe wasn't exactly verbatim, but it was something along those lines. And I was like, that was my first thought too. And then I realized like, I can't think of anything that's gone to zero.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
The stuff that goes to zero is like the stuff that, you know, you put gas on the fire and you try to grow faster than you can. That stuff goes to zero. Like stuff that, you know, like this long tail, been around for a while, proven business model. I mean, Fireside's 2016. So we're talking an eight-year-old business at this point that's been rock steady the last three, four years.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
It's not going anywhere immediately unless podcasting disappears. And then we all have bigger problems, right? So...
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Shrinking. Yeah, I would say shrinking. But again, like, so there's different categories of SaaS apps, just what I've seen in, you know, like my whatever, 10, 20 years of like doing it. And so there's like, like one example would be like, way back in the day, we made Harmony. It was a CMS platform. Did great. I had the lowest churn of anything I've ever worked on.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
You know, it was like, I think we had two people cancel the entire, like two, three years we ran it. And one person was Garrett who was paying it because he thought it was cool, but wasn't using it. And he was like, I'm not going to get around. So he canceled, I think. And the other person, they went out of business.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And so I'm like, I've seen hosting and hosting is very like, it takes a lot to get in. Once they're in, they don't leave. And then I've also seen, you know, gauges, which is what we made to go against like Google analytics. Yeah. And that was like, I was a customer number gauges. Were you really?
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yeah. It was simpler. A lot cooler and way more simple. Yeah, exactly. It was just like, look, you care about these three things. And it was live. We had this awesome air traffic, like dropping pins. Yeah, it was cool design.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Was it like- Oh, it started at like six bucks. I think the biggest customer we had- Yeah, I was gonna say, it wasn't very much. Was maybe in the hundreds, the like many hundreds, but like most of it was pretty cheap.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
A hundred percent. It's super easy. So there's no stickiness. Cause you can be like, you can run two at the same time and see if you like it. And you can use the free trial and be like, no, I don't like it. And just take it off. So like, it's like super easy in, but super easy out. And so I've seen like both, I would say those are the two ends of the spectrum of SaaS apps.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And so I'm like, well, if you've got those two ends, like where does Fireside fit? And I'm like, it's hosting. And like, yeah, sure. It's not that hard to move from like one podcast host to another in some cases.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
But yeah, You know, if you have something that's working, most people just don't want to touch stuff that works, especially in the hosting realm. And I saw like, you know, I say growing up, geez, I'm really dating myself now. Get off my lawn. But, you know, my first job out of school was like working at this company that had hosting and email and websites and all that kind of stuff.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And I mean, just pulling in a fortune on hosting. It's just because people don't, they just want it to work. As long as it works, they're not going to change stuff, you know? Yeah. And so when I look at Fireside and I think rock solid, that's why I think it's amazing to me.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
You know, let's say it's basically not been marketed or like worked on actively, like aggressively, maybe in two year and a half, two years, two and a half years. I don't know the exact dates because I don't. This is a different situation than like a typical acquisition where you would do intense due diligence. I'm like, I know the person.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I know the person in between that person and me, which is, you know, I know Dan, I know Garrett, and I know Garrett worked on it for like a year and a half, a couple of years ago. So he knows it well. And so I'm like, there's confidence in the code. A hundred percent. I'm like, this is not getting into a mess. I don't need to like, you know, select Count Star, the number of podcasts.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Exactly. So, all those things make it rock solid for me.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yeah. So we're super conservative. So like, I would say like a lot of people are like, Oh, like being an entrepreneur is so risky. I could never do that. I couldn't start my own thing. And I'm just like, I'm the opposite. I'm like, it's the easiest way for me to reduce risk. Cause I'm like, then like you can control things.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So, so for myself, when I look at like, what are we going to do with Fireside? I'm like, initially, like, we're just going to let the dust settle. So it's like, let's update some software. Like it's on older versions of Ruby rails. Again, just, just boring stuff. Let's show customers that we care. Let's be fast responding to support. Let's help people. Let's actually actively market it.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
That's, I think the biggest thing that nothing has happened with in the last, you know, like let's say two years is that there's just no marketing. And so I'm like, that's one of the reasons why one of the people that I want to make sure was, was in it was my friend Chris. Cause I'm like, that's what he does. He does marketing.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And so like, we'll get, you know, an email list going, we'll get like, you Things when you sign up where it's like, here's how you can better use us, like the normal things that like every SaaS app basically does to kind of hopefully increase engagement and usage and stuff like that.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Like there's a lot of low hanging fruit that I think we can do because it's kind of just sat in and in an awesome way, chugged along. And so I feel like that's step number one is like the rest of this year is probably like, look, let's stabilize it. Let's start building some trust back up that we're going to do things with it and talk about it.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
and like get to where we can start moving more quickly. And then, you know, next year probably be like, okay, here's some new features and things like that. And so as far as like what we have actually picked out to work on and stuff, we've definitely got some ideas. I wouldn't say we've like said, this is what we're going to do first. The goal is not all in.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
The goal is not like, I'm just not that again, I always have like two or three things. So my goals never be all in my goals always, which has always felt wrong because everyone's always like, you got to focus on one thing. And if you're doing two things, you're stupid, you know? And I'm like, I can work at 110% if I do 80% on this and 30% on another, but I can't work at 110% on one thing.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I just can't do it. It's boring. I just, I get, you get locked up once in a while on an issue and you, you know, your brain's got to process that in the background. Sometimes there's just no way past it. And so then I can just move on to another thing and it's like my brain, let's go. And then it can solve that other thing while I'm doing something else.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
It's not full multitasking, but it kind of, I find it, it's helpful for me. I'm able to kind of stay more engaged in things for a longer period of time because there's more things to keep my brain busy. So, so it's not an all in thing. So Garrett will be a couple of weeks on box out a couple of weeks on fireside.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I'll be, you know, like my hours that I've, you know, worked with my partners that they're okay with me doing on box out every week. And then I'll, the rest will put towards, you know, fireside and flipper and stuff like that. And then the goal is definitely to grow it. Like I would say conservatively, um, You know, like I've never worked on a SaaS that hasn't grown at like 20% consistently.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And so I'm like, you know, maybe Fireside's the first where I can't do that because there's just so many people in the space. I have no idea. We'll find out. But in my head, I think 5% is totally reasonable. And, you know, at that rate, I've done the math based on, you know, the capital we started with and we financed a lot of it. Like based on those two things, like I think I can have...
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Even at 0%, you know, we could pay off the loan in, you know, five years. At, you know, 15, let's say 5% growth. At 5% growth, we could pay off the loan in like four years. At 10%, it's like the end of year three, you know, whereas maybe it was the middle of year four at like 15%. It's like three years and it's paid off, if we want to. Again, from free cash flow.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And that's with taking money out of the business to pay ourselves some money as well. So that's like, if we can just grow a little bit and take a little bit of... So let's say, whatever, we have... You have $100,000 in free cash flow. You do some amount each for some salary to work on it, and then you take out some more. It has more than that, but let's just say it's that.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
It's easy to do some math and say, okay, we're going to take 50% out for the people working on it, and the other 50% will go towards... dividends and paying off like the loan early. So that's kind of like how we look at it. We're like, look, we don't have to be full time all in. We don't have to beat Transistor, Buzzsprout, any of the other, you know, whatever.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
There's a million out there that do this kind of stuff. All we got to do is like do the things we know how to do on every SaaS we've ever worked on. And the likelihood of us growing is good. Perhaps that's naive. Perhaps that's just like 20 years of experience and it will be accurate and it's not naive. I don't know on that.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I probably need to come on in a year or two years and then we'll have a better... Yeah, six months, we'll have a better idea. But that's kind of the process for us.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So like, I'll be, you know, part time on it, Chris will be part time on it, Garrett will be part time on it, as it grows, which I believe it will any any good software, you keep improving, you keep listening to customers, you keep solving their problems, you keep telling them about what you're doing, that grows, I've just never been on a team that does that, that the software doesn't grow.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And so assuming that's the case, we'll just go more and more full time on it. And at some point, it will be the only thing and then we'll probably bring on you know, more apps. We'll try and find more to actually go out and do the same thing with. I think that's kind of... Does that kind of answer the question? It's like, it's very much like a lifestyle chill.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Like, I have a Google Doc that I made at the beginning and I was like, this is what I want to do. I showed it to every person that was going to be involved. I'm like, are you... This is what I want to do. Do you have any changes? Are you cool with this overall? You know, and the number one thing is calm. I'm like, I want calm. I love calm. Like box out is calm. It does very well.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
It makes lots of money. It pays lots of people's, you know, bills and supports their families. And nobody's stressed out, you know.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
freaking out that that's totally a possible thing so I'm like I just want to apply the same thing over here just because of structure wise it just it just made more sense than trying to like roll a whole bunch of things in something over there on the other side so mm-hmm
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yeah. So, I mean, I mean, price wise, the multiple on profit was less than that. It was probably more like two and a quarter or less than that. And again, it's because like this is a massive credit to Dan. I want to give him props because he could have, you know, like. just waited and just collected checks.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
He could have tried to get a higher multiple for somebody that's going to harvest the customers. He could have tried a lot of different things. And he was like, I want the customers to be taken care of. A lot of these people are my friends. A lot of these people I've served for a long time. And he's like, I don't want it to just go away.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And so that I think was a big benefit to Garrett and I and the others is that we could come in and say, look, this is what we're going to do. We're actually going to try to grow it. We're going to make it better. We're going to take whatever, your baby, and we're going to hopefully, you know, help it continue to grow instead of just to sit and slowly kind of decline.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So, you know, multiple wise, he gave us a much better multiple than perhaps like, I mean, if any private equity company or somebody else came in, they would definitely have given probably a better multiple. He had better offer that he turned down before us. So I think it was truly like, he's like, these are the right people to run it. So I don't have a great example of like,
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
here's how you figure that out. What I've always done is like, you know, it's basically napkins.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
It's like, look, you have this much in revenue and you have this much in profit and you got to just look at the business and say like, is it fair to just look at the profit or is it, you know, should I look at the revenue and then, cause I can cut the, you know, the expenses and make the profit larger or like, it's kind of a holistic thing. It's just like, look,
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
OK, if it's at, you know, X hundred thousand and the expenses are like 20 percent, the fixed expenses of no one working on it, just the servers and software to make sure it's up and running, you know, 10, 20 percent, whatever it is, then you can say I've got the rest of that 80 percent to pay debt service and also to like pay people to work on it or pay myself to work on it.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
or any of those kinds of options. And if I did that, I've got this massive spreadsheet with all these adjustable variables. And I learned these like really cool functions, thanks to ChatGPT, where I was like, how do I amortize a loan over 15 years in an Excel function? And it's like, oh, well, you need to use PMT. And then like how much principal is left if I do this?
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And like, so I used all those things and I basically got it to where I could say like, okay, if I grow 0%, negative 5%, 5%, 10, 15. And I'm conservative. So I'm like, I'm not going to say that I'm going to grow 50%. I don't feel like that's going to happen. I'm like, realistically, we're going to put in a good five, 10, 15, 20% effort.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And I think we'll get it out of there, you know, as time goes on, but there's not any, I don't feel like there's any fancy formula. I don't feel like probably other people do that are more experienced for me. It's just like, I looked at it. I'm like, it seems like a good business. It's built in the way that I would run a business. Very low expenses, very high profit margins.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
It's recurring revenue. I'm looking at all those kinds of things. And I'm like, why would I say no? Other than maybe I'm too busy. But I'm like, it has money to pay people to work on it. So it doesn't matter if I'm too busy, really. It really just matters, can it afford to pay people to work on it? And then it's just a matter of like, do you have the money or the...
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
The financing options or other things like that to make it happen. And again, because of my fortunate past, I've got some of that stuff lined up. And so I was able to finance this. Because I never have financed anything from a software standpoint. And I was like... Let's figure out how to do that. That sounds fun.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And I learned a lot, you know, over the last two months of like how to do that, you know, little weird gotchas from the bank, like things like at the very end, we had to like change ownership percentages and things like that, or other people were going to have to personally guarantee beyond me and which I did not want. I wanted it just to be my risk and stuff like that.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So yeah, that's kind of like the longer meandering answer is like in general, SaaS apps that are, let's say under a million,
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
in revenue are probably worth you know two to four times like profit like that's or like seller discretionary so it's like anything that the seller would pay themselves that plus the profit they're probably worth two to four times that if you get bigger if you get to like one to five million then you can get you know like i mean uh you know like box out has had offers you know hand i mean very comfortably in the six and a half range that we've turned down
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
we had some stuff in the nine times range where we're like of revenue, not even profit, just of revenue. And we're like, okay, well, yeah, we would say yes to that, but it didn't quite work out. You know, like, so I would say like in that one to 5 million range that then, you know, you get your multiples can go up a little bit.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And then if you get in the five to 20 million range or the 20 plus, you can get into 10 X really easily and higher multiples. Those are like Just like if you ask Chachaputee, that's probably what it would say is something like those ranges two to four.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So like two, if it's not growing, you know, four, if it is growing when it's under a million and then, you know, one to five, there's some multiples in there and probably people would would argue with some of those, but that's a general thing that I've seen.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
The slowest part was the bank and, and like stuff like that at the end, the attorneys and things like that at the end, the part of like, are we going to do it? And how much are we going to buy it for was like a week. Like that was like really quick. It was like, I talked to Dan once, uh, we hit it off. We, you know, enjoyed each other's companies and stuff like that.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Just phone call, nothing fancy for like an hour on a, I don't know, Saturday night, Sunday night. I don't remember props to my wife for all the extra time she did, you know, single parenting while I was doing phone calls and stuff on this, but we talked and I was just like, and then he sent me all the info.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So I've looked at a lot of PNLs over the years because of box out and because of due diligence and stuff there. So I was like, I'm comfortable with that. And I looked at, I was like, I think this is what I would, I would feel okay with the amount we ended up at. It was like, I'm like, I'm a nervous guy. I'm run the foot, you know, run the ball out in the fourth quarter and the football game.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Like I'm not aggressive by any means. Like the whole reason I have multiple things is in case one of them goes bad, like I just diversify everything. Like I, so yeah, I, From that standpoint, I was like, I'm okay with this number. Are you okay with this number? And he's like, yeah, because it's you guys, I'm okay with this number. And so we got to that and we're like, okay, cool.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And then from there, it was like, okay, who's going to be in and out of the company? How much ownership are they going to have? how much capital they're going to put in for the ownership and how much is going to be work-based and all that kind of stuff. And then is it a separate company? Is it a stock sale or an asset sale? Is it like all that kind of stuff?
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And then, you know, fun things at the end with the bank where they're like, oh, FYI, if someone has 20%, then they have to also personally guarantee it. And then we have to take it back to our bank board, literally the people that run the bank and get it approved again. And that takes at least another week. And I'm like, we're supposed to close tomorrow. You know, like.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yeah. So stuff like that.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So what's funny is I was feeling that, and then once everybody... who was coming in came in and I knew all the amounts and stuff, it won't be the biggest risk, technically. Like technically BoxOut would have been. Because BoxOut was, you know, I gave them straight cash at a pretty good evaluation. And that was definitely, now that was also when I had the most cash.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And so it was like maybe an easier decision. This feels riskier. But amount wise, it's not as risky. So like technically my part was mostly the collateral and the organization, the deal structure, everything. And the stuff that like, if I hadn't done that, then it wouldn't have happened. So that was my part.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And then each of the other three people that are in it, Garrett, Chris and Steve, like all are putting capital in either this year or next year based on, you know, the terms we've worked out and stuff like that. And that will get the finance amount basically like lower than what box out was for me. And so and again, for me, like what I what I brought to the table is the collateral. And so
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
For me, it's like I have a lien on my house now. I use my house because I learned that you can get 80% for your house. My house is paid off, fortunately. So you can get up to 80% of the value of your house, whatever it appraises for. Snap your fingers, the bank will give you a loan for that, a commercial loan. Land or farmland, I have some of that. I was going to do that at first.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
They're like, I will only get 50% to 60% of that. And I was like, oh, well, that might not work. So it's kind of interesting to see what banks will do based on the assets that they're really comfortable in dealing with. Cause they will not do it for software.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So if you do like a, if you want to do it just based on the software and then basically you have to personally guarantee it, you don't have to put up any collateral, but you have to personally guarantee it, which is the same thing kind of. And then you also, you have to do like an SBA loan and SBA loan is like a ton of extra paperwork. And it's like 11% interest rate.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So it's like super high interest rates, like prime plus two or something like that is what I was told. I just did a commercial loan with collateral. My house is collateral. And yeah, I ended up with below six and a half percent. So like half the interest rate for me. Additionally, an SBA loan, you typically have to pay off in five to 10 years. So your payments are, they go way up.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Whereas like, again, my collateral, they're like, what do you wanna do? Like 15 years? Like, I'm like, yeah, that sounds good. Like I'll do a 15 year, I'll lower the payment at the beginning. And then as we grow or as we stay the same, whatever it is that happens, I will just apply more to the payment to pay it off early. But it gives me flexibility because basically I can snap my fingers.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I can get some cash flow to run the app. And then the only risk is like... a lot of things go wrong. Like the market goes down, I don't know, like 70%. So then my, you know, any stock that I have is worth nothing. And like, you know, all my cash is at zero because of inflation and the pot, everyone stops podcasting or goes uses free things.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Like I can't count the number of scenarios that would have to go wrong for this to be like really bad decision. And so from that standpoint, I'm like, if all that stuff goes wrong, no matter what I'm doing, I'm probably going to be in a little bit of, all of us are going to be in a rough spot. If it gets, if all these industries, you know, collapse, we've got bigger problems.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So I was like, I'm just going to, for once in my life, like take a little bit of a bet. But I would say overall, it's not as big of a gamble as box out from like a purely money standpoint, because technically I haven't gambled anything. I've only gambled like possibly having to pay it off.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
early like myself personally and that wouldn't be fun or you know having to do that when the asset goes to zero something like that so it's like well i really made a pretty big mistake and the other guys made smaller mistakes but i don't think that will happen so i feel pretty confident that like again worst case scenario is this just keeps slowly going down
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
over the course of like six seven eight years it gives us the money back and we wasted our time like that's the worst case scenario and that's such a negative outlook on life i'm like i'm not i'm not gonna wake up in the morning to do that i'm gonna wake up in the morning i'm gonna see what i can do you know like so that's that's what kind of i don't know i i guess does that is that like the again meandering that's gonna be the theme of this but um
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Totally agree. I've watched you guys. I've watched MFM. I've watched several podcasts. people in let's say media build audiences. And I'm like, again, they like the quote. That's like, I think I put it in the post, but it's like first time founders focus on product. Second time founders focus on distribution. And I'm like, I think podcasts are an amazing distribution system.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I absolutely love them. The people I feel the closest to that I don't even know are podcast hosts. And I'm like, that's just, that's a weird thing. Like you guys have these like mega fans who think they know everything about you. And they do because it's just the, the format is, They kind of do in a way. They do. They know everything.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I think it's a great medium. I think it's a great... Like, I love everything about it. And I'm like, I've done a lot of consuming of podcasts over the last, like, let's say four years. Like, probably, again, like most people, like around COVID, it really started exploding. And... Because of that, I'm like, I wanted to do something. And my plan was like, well, I'll just start a podcast, you know?
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So I started going on like found requests with those guys. Love them. I was just a third wheel. I could hop in, you know, add some accountability. Like, are we recording this week? You know, and stuff like that. And it's awesome. I don't do any of the work. I don't have to pay anything. I just show up and talk. This is like my ideal job. And I'm like, so that's cool.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And then I was like, well, what if, you know, when Fireside dropped in, I was like, what if it's just bigger? What if I hosted them too? I'm noticing that FunnerQuest is a transistor podcast.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And, you know, I love Justin. I mean, Justin, he got me back into indie stuff. Like, I was completely out of indie. I was at GitHub, you know, and even then I left and, you know, did BoxOut, but I was still not, I was not in the indie space. I was not doing other stuff on the side, like... And then I started listening to Mega Maker and some of the other stuff he did.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And I was like, heck yeah, why am I not doing this? I should do this again, you know? And so again, for me, I'm like, I want to now have a podcast. I want to have my own. So I think Garrett and I, you know, we're going to start our own, you know, fireside podcast.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And it's going to be like, maybe two, maybe one is like the building of, and one is like, here's how to better, you know, like we interview other podcasters and talk to them about their setup, what they do, what's different, like all that kind of stuff of like, things that teach people how to start or how to get better or how to improve.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
But then we also, I feel like the thing I'm passionate about, which you can hear when I'm talking about it, is like, I'm passionate about the company side. I'm super fascinated about, like you said, with the hub and spoke of like, now we have like a nice chunk size business that can be kind of like a starter. And it's way easier to buy that than to build that.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I mean, I'm building that with Flipper. Flipper's like, you know, five figures, mid five figures. So you're talking like, that's of like... Again, partial work on it and stuff like that. But it's not big. You know, Fireside is like more like mid six figures, you know, box out seven figures and stuff like that. So I'm like, I've seen the ranges in there and stuff.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And I'm like, it's way easier to acquire something than to start and build that from scratch. It just takes a long time and also a lot of like right, right decisions and stuff like that. So, so yeah, I think it can definitely be that kind of centerpiece. And then it'll, because we have, you can't have a podcast host and not have a podcast, right? Like you, you have to, I think it's actually law.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
It is. It's law now. Yeah. I passed at least in California. I'm not sure about California.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yeah, I've watched it.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
It's familiar, but it's been like years since I watched it.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I take that as the highest compliment I do. Because, like, I don't, again, there's other people that, like,
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yep, it could have been worse. But yeah, I feel like, you know, I don't know the best way to answer it, but I feel like, it's not even really a question, but more it's like, I very much appreciate that sentiment. It might, I don't feel like I have golden touch, but I feel like I am very conservative and methodical. You know, my favorite quote is that like, you know, consistency beats intensity.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Like, I don't have to work on this 60 hours a week, you know, for three weeks. Like I can work on this, you know, X hours a week for five years. And I can just keep doing that because I love the process of building software. So that's like my, I guess, my advantage. And that's why I'm not really worried about it. It's like, I like the process of building software. I like talking to customers.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yeah, sure. So basically I was in RubyConf in New Orleans and it was, you know, hotel and conference and bar and all that, like all together and just walked into the bar. And I'd been friends with Chris Wansroth from GitHub for a while. And I saw the year. Oh man, 2011. Yeah. Yeah. Actually, it's easy for me to remember.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I like solving their problems. I like building stuff and I like charging them money for it. And it's not going to, I'm not going to build the next GitHub. I'm not going to build the next of any of those kinds of things. And I don't even have any interest in that, but I'm very happy to build something that's like someday is five, 10, 15, 20 people max. And everybody's really stoked.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And we just try and pay everybody more every year. You know, like that, that sounds awesome to me. So that's what I want to kind of do next is that kind of thing. I don't know how long it'll take or if I'll succeed, but.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
It's possible, but I've worked at bigger companies, but I guess I wasn't at the top in bigger companies.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Really? Yeah. I mean, box out was literally four people well past a million, like four people, maybe five people, you know, like some, some help and support and stuff too. Like you can, there's so much leverage if you can write software. And the key is finding people who can also either depending on,
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
know the the plans can either market it if it's lower price plans or sell it if it's higher price plans you know like i feel like that's it's just build good software and then have one of those arms you know you got that wrong build very good software yes very good software yes buy it or not we're not beggars parks and rec huge fan there you go what's the right number of businesses to own in this holding company
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Well, I think it's just based on the number of people and the amount of work that's necessary. So again, I don't believe every piece of software requires full-time work. I don't think that that's a thing that you have to do. So I think the right number of businesses is how many can we work on based on the people that we have and the revenue that's inside of it.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So if we have the revenue to support... Three people, whatever, halftime, that's what we'll do as soon as we have the revenue to support more. The people who are halftime will move off of other things, aka box out, and they'll move up on this and I'll replace them at box out with somebody else. Because they're owners, I want owners in the company working on it more than randos.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So that's, I think the answer is basically, I mean, having done it now, I'm like, oh my gosh, I want to do it again. But Garrett is like a very good anti-force to that. He's like, dude, can we let the dust settle on one? Can you just like calm down? Because it's really cool. I think it's really neat to find like a good, but I think it's also very hard as well. So we got lucky.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
We had one drop in our lap. That's not going to keep happening. But maybe if I talk about it, maybe it will. I don't know. We'll see.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I have some leverage left on my house. Uh, yeah. So let's.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yeah. I mean, they would just not for as much.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yeah. So there's other things, but again, if you can get something and you can get it for the right cashflow and then you can, I have again, so fortunate to have worked at GitHub. I have so many friends that from that era that I know would love to work together again. And I'm like, it's not hard for me to find people to work. It's harder to build the business to support more people to work.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
You know what I mean? So if I can find a business that's just there, I'm like, yeah, I could hire people that are founder energy to start running them if we can capital-wise make it happen. The goal is just to do it all in this roof and align incentives. That's even like Flipper is currently in a separate company, but we're going to merge it in soon.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Not that we're into medical things here, but I had three hernia surgeries that year. Gosh, that would make it easy to remember. It sticks out. Yeah. It's like stuff that is not normal. Which one of these is not like the other years?
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Somehow we'll figure it out without messing up taxes and stuff like that, because we want all the incentives aligned. And like Chris didn't want to merge speaker deck in right away. And that's fine. I gave him all kinds of crap about it. But I was like, you know, you keep your little thing over there. But I'm like, maybe I won't help you anymore. You know, like I do.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I'm just like, you know, teasing him because I'm like, part of me is like. That'd be cool to have that in also, because now you've got like speakers, you know, and presentations and stuff like that. You've got that's media. You've got media with this. You've got software here. You've got lots of advertising space across all of them. You've got lots of distribution.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And so I could see that working, but we can also work with misaligned incentives and we can say, hey, I'll build your new platform. advertising system that advertises Fireside on, you know, anywhere we want and advertises this. And if we can figure out, you know, again, we'll have all that in-depth data. We can say, oh, this is worth X to us.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
We'll give you this instead of the ads, you know, the ad money you're getting right now. So there's still things we can do. But I really like this idea of everyone aligning incentives in one company and just we get multiple shots on goal inside that company as well. I think that's just really cool.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I haven't on this one and maybe I will in four years, five years. I don't know. But like right now, For me, I have this, again, it's just another theory that I've sold too quickly, like in the past. And so there's a side of me that's like, what if I didn't sell Harmony and Gages and all those things? Because in some ways, a lot of ways, they were way ahead of their time.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
They're pre-plausible, pre-fathom, pre-all these things. I was going to say, plausible is killing it, you know? Right? I mean, you can't tell me if Gages wasn't still around and we were working on it. I mean, it's around, but it's some PE firm owns it, so who cares? But like, if we... didn't work on it for the last 15 years, you can't tell me that it would not be killing it.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
It was brutal. Yeah. And they told me the last one, it was like so bad. They're like, you're going to be back in five years. I'm like 10 years sober from hernia surgeries. So yeah, I'm living on borrowed time right now. But anyways, we were like, I went into the bar. I saw Chris, we started talking. We were just talking about like GitHub, which is, you know, maybe like 40 people at that point.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I just, I would not believe it. I feel like it would be,
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
would be killing it and harmony as well i feel like harmony was way ahead of its time on its template system and the control that it gave you and the ease of use for like people that are not devs to put content in and stuff like that and i'm like i just there's a side of me that always wishes genuinely that i could a b test my life and see which path because i like control and i like return on investment and i like you know having an impact and it's really hard to do in a big company
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
obviously things went great with GitHub and, and stuff like that. But I'm like, I'm just better in small stuff. Small pond is my, that's my, my thing. So I'm like, I'm really curious. So I don't know. I don't know. Like maybe it would make sense to like go bigger or to do other things or all that kind of stuff. But I'm like, I know those other things.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And so on this, on this instance right now, I'm like, I don't want to sell. I want to, as long as I can, I want to just like be like a buy and hold and, And also the last three weeks I've been reading Warren Buffett. That's probably the, that's probably part of it. But, but I, I formed the thesis, you know, before that. So now I'm just like, okay, well, what does he do?
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Cause that's, he's a very notorious buy and hold kind of person. So yeah, so that's, that's kind of it. I could be totally wrong. Maybe I am just like zero to one or zero to 1.5 or two and sell. That's entirely possible. But I kind of wonder what would happen if I didn't. And I'm like, I don't have to sell right now.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And then like the stuff we were doing at Ordered List. And there was five of us and we, you know, talked for a couple hours and then went our separate ways. And then he ended up messaging us and we connected in South Bend. And they were like, what if we just, instead of like, you know, me personally in investing or something like that. What if we just acquired you guys? And we're like, cool.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And they just made a glass one. Like literally it just came out. Oh, that's so cool. Yeah.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yeah. So, I mean, you don't have, but I view like here, my obsession, I think the last, let's say three or four years has been cashflow. Yeah. Cause I'm like, like I've seen the, I understand multiples and exits and stuff like that. But I'm like, if you can create a lot of cashflow, like then you can, you know, you can pay people to do the work and keep the cashflow coming.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And then you can do less and less on it in theory. And so like, I mean, I've definitely seen, you know, I don't work as much on box out as I used to. I mean, that's, that's a true thing. I feel like, Once you can get the cash flow, then you can pay people well to work on it. And they're probably better than you at those specific skills anyways. And so it's fine. Maybe they're not.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
That's entirely possible. And I'm picky, so I don't know. But we have a couple of people in the development seat now at BoxOut that are doing things. And so we're... You know, we have to obviously that it's not just a press a button and receive code. It's a lot of work to like train people the way you do it or things like that. But I don't think you have to. Here's the thing.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
My kids are like nine and six. I'm not doing anything. I'm going to be tied to a location generally while they're in school and things like that. So I got like at least 12 years for sure. So again, maybe in 12 years, I might come back on, you guys will still be here and you'll, you know, everyone will have the fully gray beards.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And like, at that point I'll be like, no, I sold, I'm done. Like I, you know, that's possible.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
You are. I think it's amazing. I mean, that's one of the things I talked to Adam about. I'm like, how do you keep doing it? It's amazing. Like, I mean, I'm five years on. Just keep showing up? Yeah, I'm five, six years on box out. And I'm like, you know, it just kind of runs and it does great. Because there's a lot of people involved, you know, like we had our first Christmas party.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
We had never done a Christmas party. We had like, I don't know how many people, 20 people or something like, and we flew people in and all kinds of stuff. And we all got together and ate food. And so it was awesome. I was like, dang, this is fun. You know, I don't know about, you know, GitHub summit size, 50, 100, 200. I saw that path up to a thousand. I'm just like, that's crazy. That's a lot.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yeah, that sounds good. So we did that and then worked there for seven years and then perfectly had a daughter in June of 2018 and went on parental leave and GitHub was amazing. I got five months off to full pay, do whatever I wanted. It's a long time. It's amazing. Yeah, I got four months with my son, who's like three years older. And I thought that was just like unheard of.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So I like this idea of small things that can do well, you know, like the below, you 2 million. If they, if they go up like over that, that's fine. But, um, I think there's a lot of, there's, and there's other companies that are doing this too. Like I've seen like third South capital. I'm actually talking with Justin, the like, who's in that, the button down guy next week.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And there's some other people that have reached out smaller or bigger than that. Uh, or I don't know what size they are, but like what I've seen is they do some bigger deals more in the, like, let's say two to 5, you know, million, whatever range kind of stuff. Um,
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
But like below PE, like PE is usually like they'll sniff around in the one, two range, but like they don't get super interested and excited to like five or ten usually. But I'm just I'm seeing more people kind of move down market because they're realizing, hey, you can buy stuff there and then grow them. And just you get multiple arbitrage.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
If you are going to sell it, you can buy it for a two to four X and sell it for a four to six X if you can grow it. So it's just interesting. I don't know. Again, I have no idea. This is my current thesis right now. I'm just blabbing. Even as I'm sitting here, I'm like, do I believe all these things? Like, I'm not entirely sure.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I actually love it. I think it's great.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
some assurances and so you can kind of gauge where you want to go next that's a intended pun there yes and i think like a big thing too is that like at ordered list you know they're like there was steve and i but we had three guys working with us and you know the github stuff happened and that was all great for them and i was like that's cool like that's really cool i was a part of of like helping someone else obviously they did the work and stuff like that too like but i'm like that was a neat thing and now i'm in box out and you know steve and i have been through this before
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
but you know we got two other partners and i can see that like again all the four of us together have created something cool it's cool that like we've helped enable it because we know the software stuff you know and so i'm like it's almost like okay well who who are the next group like and so it's and that's where like one of the things i think that's kind of driven me a little bit it's just like who are some like other people that i'm really good friends with that like
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I would like to also be in like a, on the lily pad with, or whatever, you know? That's right. To bring it home. Like, who do I, I want to help them get to a bigger lily pad or whatever. I think it's cool. And so, you know, if I can help with people that I, who do I want to spend time with? You know, I'm going to work. I love the process. I'm not just going to like stop. I love building software.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So like, who do I want to do it with? And how do I find things that can pay for them so they can do it? And it makes it worthwhile for both of us, you know? And I think that's even the fireside deal. That's kind of what happened. It's like, it's worth it for Chris. It's worth it for Garrett. It's worth it for me. It's worth it for Steve. It was worth it for Dan. Everybody kind of wins.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And I think there's more out there like that too. It's just a matter of like letting the dust settle on this one. And then, you know, we'll see from there, but at least if I talk about it, then people will hear it. And then if it happens to them, they'll think of me and maybe, maybe it will be something that I'm like, okay, yeah. that's a rails app. It's very stock and standard.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
It's making good money. You're tired of it. Or maybe like, I like you and you're doing this and like, why don't you just merge our, you know, merry band of SAS artisans or whatever? Like, so yeah, I just think there's some cool stuff out there for that. So.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
My dad, you know, I was born at like, whatever, 3am. He was back at work at 6am on the farm, you know, like, so that brain can't even compute. And so yeah, we... had my daughter and then two days later they were like, there's rumors about the Microsoft stuff. And then like three days after that, it was like announced. And then basically I went on leave.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And then I, my last day of leave, I had a Friday GitHub and Microsoft closed the acquisition. And that Monday was my first day back the one after that. And I was like, sorry, I I'm out. And so that it just timing wise worked out. Like they asked me, I was like, I was totally planning on coming back. I was, I had no intentions. Cause I'm like, you never know what's going to happen with deals.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yeah, that's definitely a thought process is like, how do we, you know, whether it's cross, cross sell or like any of the other, I mean, there's tons of different, you know, business acronyms and words and stuff you can throw out for that kind of stuff. But that's definitely in the thought process is like, uh, like the rising tide lifts all boats kind of all lily pads.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I'm not going to like quit in the middle of leave and have a deal and not go through or things like that. But yeah, so we were 45 through 50 early acquired kind of like a strike team. And then we all went our separate ways and worked on different things. But I think it worked out well for both sides. And so that's kind of like the very fast forwarded version of it.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I think that that's a thing that is a real thing. So especially if you stick to rails and you standardize really heavily, and that's, that's the thing that like,
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
steve and i have always done with all of our previous stuff is like we're super standard and like how we do all the stuff you know it's like it's always bootstrap it's always this it's always that even if it's like well we might be curious about tailwind or other stuff but we're like you know what we're standards it's it's not about in individual enjoyment it's about you know across the board all the things that we're working on how do we make that enjoyable and fast
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So there's definitely parts in bits that we share and stuff like that. And I can see that big time for this kind of business as well. Without intertwining them so much that they would be hard to sell if there was some scenario where we wanted to.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
They're not, no. Yeah, no. They're not. Yeah, that would be fine. But if it was Python or if it's like, again, I don't have anything against Elixir. I like Elixir. I think it's cool. I've tried a bunch of stuff. I have a ton of smart people who like it. I just like what I'm doing. I don't really have a strong desire to like...
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
change it what i'm more fascinated with i'm less fascinated with tech and more fascinated with like how do i create more like jobs to work with people that i like and that i want to see like you know not have like not have uh what's called laid off not be laid off or not get fired or not have like sure how do i create more of that kind of stuff is just more interesting to me than than those other things now maybe i should just go into one of the other ones and like
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Hire somebody to do that. But I don't know those kinds of people. I don't really know that many people who do whatever these other frameworks. So it would be harder for me to like figure that out. So like right now, and maybe in the future, that's less of an issue. But right now it's like, you gotta be like, you know, ICP, like ideal customer profile. And the ideal customer profile would be like,
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Rails app, Stripe, you know, even Bootstrap. Like Fireside is Bootstrap 3. It's like, well, I've done the 3 to 4 upgrade. I've done the 4 to 5 upgrade. I've done all those things. I know it's 2.7 on Ruby. I know how to get to 3 and all the Quark stuff. And then I know how to get to 3.1, 3.2, 3.3. I know how to get Rails up to 8, all that kind of stuff.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I'm like, it's just, it's a straightforward path to like stabilization and then iteration.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And then done box out like kind of the last box out sports the last four or five years since then. So 2018, yeah, it would have been right at the end of 2018 when I moved on to that.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Maybe you have me thinking now, I don't know. I'm you might, I'm definitely processing live and I'm like, in terms of other languages.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And I would have to have a good team probably already, or I would have to have a friend who knows the exact technologies being used. Sure. That could just step in, you know, like, cause the marketing and things like that don't matter. You can standardize that stuff at the top of the holding company or whatever.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
It's just the tech that I would be like, I'd want to, I'd want somebody again, like I was listening to a podcast on acquiring minds and it's like a guy who buys manufacturing companies. And it was like, I mean, I was just like not in my head profusely the whole time.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Like first podcast ever, I'm probably going to listen to a second time and maybe a third time because I was just like exactly what this person is saying. And it was all about like, he's like, look, I'm not going to buy a manufacturing company that I can't step in and like run the machine if I have to. Like, he's like, I just want to, All the way through.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I want to know that it worst case I could go in there by myself and I could I could keep the thing going, you know, like like he's that conservative on stuff. But yet they're compounding it like, you know, 20 percent or or or more. They're doing great in growth and all that kind of stuff. And so I'm like, that's that's in my head, I guess. In my head is like I should be able to step in and like.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
if push came to shove and like run the thing. And I just, I don't know, maybe I'm too old, too many gray hairs to like totally switch languages and frameworks and really feel like I could be, it would take me some time, I think, to be successful doing that.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I think I would, I would do it. I would just, I would have to learn more about how people do that. Like, and even in that, again, that podcast episode that about like buying five, I can share the link later or whatever, but it's like buying five, you know,
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
manufacturing companies in that scenario that guy was like they do like the kind of like a PE model where they like basically they're like look we come in and we run it and like one there's you know six partners in the group and each of those partners will personally guarantee one business And so right now they have three guaranteed. And then they have, when they do that, they do two things.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So one, they charge a management fee to the business based on EBITDA. So like if, you know, they buy businesses that already have good profit margins, they take a slice of that profit margin and for everyone who's in the management group. And then they'll also do, you know, like, whatever first 8% preferred return in the event of a sale, you know, goes to the investor.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And then after that, it's like split based on, you know, equity and all those kinds of things. So And they bring in basically different people in every single deal. So I wouldn't say different people from the standpoint of like, well, you know, Adam's in this deal and Garrett's in this deal or stuff like that. It's more like we've got five people each putting in like 100,000 or 50,000.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And so now we have, you know, whatever, 250, 500,000. And then we're going to personally guarantee do an SBA loan for the other half. So their debt, you know, to like whatever ratio is basically like half.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yeah, I did. I piped it through before. I just had a gut feeling. And I was like, add some mumbles and some ums to make it look real. That was in the prompts.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Cause again, then it's like, well, if the business went all the way in half, you'd still be able to run it, which is, it's pretty rare for a business that's been around for, they stick to like, you know, 60, 30, 60, 80 years, like, you know, 30 plus employees. So they know that it's like all the knowledge is not with one owner in a 10 person company. or things like that.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So again, a different scenario here where we have software and leverage and stuff and it's less of a concern. But I'm like, that idea is really fascinating to me. And then, so then, you know, the group, the six, each have a share in each of the companies they acquire. One of them runs each of the companies they acquire. One of them personally guarantees, not necessarily the one they're running,
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And then they also kind of, for lack of a better word, they shard their investors across all the deals as well. So no investor is heavily invested in one of them. And I'm like, I actually really like that model. I think that's sick. Because now they're doing the SBA loans, which means they can personally guarantee but not actually put up the collateral.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So you don't run out of collateral and run out of money. But I'm like, I don't know all that financial stuff yet. I haven't done any of that. So I'm like, I'm just going to start simple. And I'm like, look, I got some friends. They had a little bit of cash too. I got the collateral. Let's put it together. Make it look, you know, like a three to five year payoff.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
If it's an eight year payoff, and we take more cash out, that's fine. You know, it's just like, ideally, I don't want to have my house on the hook forever, you know, or maybe I pay off the loan at some point, like, let's say box out does sell for some reason, like that we we're not planning on it. Now. We're not talking to anybody. We don't have any interest in that. But like,
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
If somebody came along with the right price, we'd be like, sure, that happens. Now I've got some cash flow. So maybe I pay off the loan, get the lien off my house, and then I loan it back to the business at a lower interest rate or something like that so that the lien is basically gone from my house.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
But there's still some amount of leverage of using other people's money to make money, which is kind of an interesting concept, I guess. Yeah. Again, I'm all a rookie. I don't, I don't know any of this stuff. I'm just flapping the stuff that I've been researching for, you know, a couple of years and then heavily for a month or so. So I don't, I don't know, but that's just what I think in my head.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yeah, I think it's, there's a lot of ways to get capital. And it doesn't hurt, like, I mean, I probably have, I mean, I've got the GitHub, you know, founders, other people in my phone. I mean, I could text them, but I'm like, I don't need to.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yeah, it was not hallucinating, unfortunately.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I don't know. And even just for the reason that the, again, I don't want to keep going back to the other guy, but I just, it's fresh in my brain. Cause I just listened to it and it was like, yes, I like what you're doing. I'm headed to the ER cause my neck hurts, but like, cause I've been nodding my head, you know, profusely, but I'm like, I like this again. Exactly. Pop another hernia.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
But I'm like, I like that idea of like not running like a fund because a fund has to receive the capital and then deploy the capital. And so you're kind of under constraints because you've got to deploy the capital in a certain amount of time. But that means you're going to maybe have to deploy the capital into a deal that you're like not super excited about because it's like, well, it's time.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Otherwise, you know, the fund is going to run out, et cetera. Whereas, you know, this model is like, look, we get people to commit, but then they don't have to give their capital up until the deal is actually here. And we know it's a really good deal because we have just been, you know, vetting them profusely.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And so this is like, yes, this is, you know, their range was 500,000 to 2 million EBITDA. They're going to do X multiple and they're going to, again, shard their investors, shard their individual personal guarantees. And I'm like, that's just a really cool model. If you can make it work, it probably takes a lot more smarts than I currently have, but I think that's cool.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I like that idea of like, yeah, that, that process.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yes. That I'm, I'll be, I'll be super interested in. And that's even why, like the first thing I did is I reached out to Adam cause I, not even about investing, but just cause I was like, he's in podcasting, you know, and everybody knows you guys are killing it. So, you know, I was like, well, Hey Adam, like, no, I'm just kidding. Just killing it, crushing it.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Then I was like, again, you know, podcasting, you know, this kind of stuff. Cause I'm like, he told you he was going to go to zero. You called him and he's like, this thing's going to zero. Here's what happened though. That was the first five minutes. And then by the end, he's like, well, how do I get in on this? You know, not really, not really, but kind of.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
You actually could see that story in Adam having a lot.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I take a hit. That's what happens. I definitely did that math too, 100%.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yeah. Neither of those. That's a really good thing to say. Cause I feel like a lot of people just go right to the worst case. And I'm like, that's not the common case. That's one of the best things that I think has partnering with Steve has been is he's very much like a, not a worst case. He's like, I mean, well, worst case, you just get a job again. Like it's fine.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And I'm like, Oh yeah, that's, that's a good point. I actually do have like marketable skills. So it's like, yeah, it wouldn't be challenging.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Because, again, because he wants in. If he gives all the ideas, then he doesn't have a way in.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I just look at what you guys have the distribution. You have like this massive audience. Like, I mean.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
You guys got the distribution. So, you know. All right.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
We'll talk. We'll talk.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yeah, that's a really good way to put it. That's better than, again, you get to sit there and analyze what I'm saying while I'm saying it on the fly, but that's a really good summary, I think, of it. Hopefully it works. I mean, I think it will.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I mean, I say hopefully, but I believe it will too. I honestly don't. I don't feel imposter syndrome. I don't feel like it's not going to work. I feel like I'll just figure it out one way or the other. It might take more work than I thought, but I'll figure it out.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Well, when you work at a 1,000, 2,000 person company, you just run into a lot of awesome people. I mean, it's hard not to find 10 really awesome people at a company that size. That's the one benefit of working at a really big company. If you stay at the small stuff, it's a lot harder. But again, it's conferences too. You got to show up at the conferences. Yeah.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
you show up at those and then people, good stuff happens. I'd stopped for 10 years and that's when the good stuff didn't happen. And then now I'm back on it and I'm like, it's awesome. It's amazing. I don't know why.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I did RailsConf in Detroit. Okay. So I'm in Indiana. Detroit's like a three, four hour drive. So I did that. This one was in Toronto, RailsWorld. And then RubyConf was in Chicago. So I was like, I'm doing the Triple Crown. I'm like going from no conferences since my kids were born to the Triple Crown in one year.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So the recap of RailsWorld, electric energy, the Rails Foundation just did like an amazing job of putting... this like really cool venue, partially outside, partially inside. The only problem was the bees. There was like a lot of like, not bees, but like hornets or something, you know, they just, yeah, they would not leave me alone. It was like your flies, but with like with stingers, you know?
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And then the talks were great. Like DHH kicked it off with an amazing keynote as usual. Like they got everybody kind of fired up. And then I would like to say the rest of the talks were amazing. I believe they were. I was in the hallway track the entire time and I did not shut up. I was just meeting all my old friends, making new friends. And it was just, it was awesome. It was really good.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
A thousand people or maybe more, I don't know. So something like that. So it was just, it was packed. Great energy, very low like shilling of services and things like that. It was just like lots of great people smashed together. Shopify blew it out on the last night.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I cannot even express how amazing the Shopify closing party was because they got this amazing three-story office and then COVID happened and like they just turned into an event space and it was killer. I mean, they had barbecue on the roof deck, like legit just making barbecue, putting it on sticks. I ate like 10 in a row and the lady was just like, you must really like this.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And I was like, you guys are amazing. And we became friends, you know? Nice. And I'm like, it was just that kind of, it was a great vibe. So yeah, it was really fun. I feel like there's a lot of excitement coming back to Rails as things kind of swing like a pendulum, like they always do.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yeah, that's definitely true. I mean, I feel like even BoxOut before that, that was kind of, let's say that's the first investment. I mean, I worked there, so it doesn't really count. I don't know if that counts as an investment, but I bought in. I didn't like join and then it wasn't like work equity. It wasn't stuff like that. I bought in for like 25% of it.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So, yeah, that's cool. I mean, we even had Laravel and Tailwind and like, you know, people like that. They were there. So it was good. There was a whole lot of Different, you know, it was great. It was really great. It would have been awesome if you'd been there. We did some live podcasting.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I have a couple friends there. They said it was just wet, but it didn't get hit like everything else. It's been crazy out there.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I think I have a... We might have a camping trip that weekend, actually. I'm not sure. I'll have to check. But you know what? I have traveled so much. If I leave again, I'm going to have to find a new wife and family. Yeah, it's not going to work out. I'm already going to be gone in November, so I'm at my max traveling. So you're welcome to come here.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
you know, we'll put you up in a room if you want to hang out.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Oh man, you guys, we should, we should do like some kind of, yeah.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
There's nothing, but you know what I was thinking when I was at Railsworld? I was like, what if I just invited like a bunch of my friends and did like a, you know, like, well, so we're, we, one of the things I'm in is like a real estate thing where we're doing like an entrepreneurship hub and a big building and stuff like that. We did a groundbreaking like a couple of weeks ago.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And I'm a very small passive, you know, part of it. The other people are doing all the hard stuff, but I'm like, once that's exists and there's like a nice, awesome event space that like, like I was a part of, I'm definitely having some kind of like John conf, just bring all the smart people together and see what happens. I don't know, whatever. It doesn't matter to me what we call it, but like,
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
It's just like a bunch of different skill sets and cool people. I think that'd be really fun. And then try and grow it every year. Not trying to make anyone just try and break even, you know, like just not the good stuff from less. Exactly. Yes. Like I went on the less cruise and it was amazing.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And then I've additionally worked there as well. And so I kind of saw like from there, I think I saw a little bit of like you can... I've got this post on my website that's like cushion versus flow. And it's this idea of like, you have like, you can have like a cushion, which is like, you know, cash cushion, or you can have cash flow and you can use them interchangeably to create the other.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
No, this says less but better. Yeah. But I do. I had a don't quit your day job shirt from them. It was my favorite shirt. And then it just got like old. And so now I just wear it on my way home from basketball after I'm sweaty. That's it. But it's still a great shirt. Or it says quit your day job. Sorry. Quit your day job. Yeah.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
keep your day dream we always say I'm sorry for what I said while we were parking the camper that's that's a big popular one oh yeah you have to yeah because you're always like on the phone backing up this trailer like for your left or my left get it right what go left it's always a mess
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yeah, exactly. You got at least 12 years.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And so it's just like at any given time, you have to kind of choose between which one, like, do you need a little bit more cushion? Then you can take your cash flow and you can save some of that and you can build up a cushion or vice versa. And so Boxo was kind of the first one where I was like, okay, I have a little bit of a cushion from GitHub. Like I'm not going to stop working.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I have like a six month old and a three and a half year old. I'm going to be at a desk for a while. And so I was like, what am I going to do? And I had some friends already that were doing it. They were doing well. They could use help. And so it just kind of made sense to buy in and do that. And then doing that, we're getting about the size where we're on, let's say, private equity radar.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I don't know how. they know, they just like sniff it out and they can tell. And so they're like, Oh, you must have, you know, X million in revenue. Like we'd like to get to know each other. Are you up for, you know, coffee in the Bay area? And I'm like, no, not in the Bay area, but, but I've done a lot of interactions and stuff like that.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Went through a lot of like due diligence and a lot of deal structures and negotiations. And then I started getting this
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
idea of like and i listen to a lot of my first million i hope i'm allowed to mention other podcasts on this but please do yeah yeah so i'll leave it out no big deal that's fine you can bleep it out make it unnecessary censorship there but yeah like i i listened to that and listened to some other stuff and i was uh acquiring minds and i was like what if i just like bought something so i i
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
in and out of while i'm at a box out like i've been looking at that kind of a a thing and just nothing came along that was like that was right you know like i just couldn't find the app and then i was i was working with garrett uh diamond and i was paying him to work on flipper so that flipper could move forward while i was kind of working on box out the last year and we were in kind of like a
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
A deal with another company kind of related to PE and stuff like that. And I was like, I want Flipper to be there in case something happens with that. And nothing did, which is totally fine and great. And so then Garrett knew Dan from Fireside. And Dan was looking to get out. He had kind of stopped podcasting. Use a full name. What's his last name?
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Yep. DB, Dan Benjamin. Here we go. And so, yeah, Dan was looking, I think, for a good home. Like he had, he'd went around to like, I think, and talk to like a lot of people. He's obviously well-known in the podcasting space and stuff like that.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And he was like looking for someone who could take it over, who would like do the customers right, who would like push the app forward, who would do new things, not just harvest it and shut it down. And so he mentioned something to Garrett and Garrett has been a founder. Garrett Diamond has been a founder in the past. Now I'm going to get those names every time. So I'm ready. I'm trained.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Diamond, Garrett. And so I was like, he was like, you know, I don't want to do this by myself. Like, but like maybe John would be interested. So he reached out and and then we, you know, there's a lot of name, please.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
Diamond cup Garrett.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I'm a little slow on the uptake, man. I'm not pros like you guys. Sorry. So yeah. So that's kind of like how it kind of came about. And we're like, well, hey, if we can get this one, I bet there's a lot more. Now, I don't know that we're ready to just go in there and we're not taking on outside investors. We're not making a fund. We're not going to be private equity where we
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
you know, have like management and carry or whatever and all that kind of stuff. Like we're just going to build like a nice portfolio of small things. We're starting with Flipper and Fireside because we already had Flipper. We were able to get Fireside. And now it's like there's probably a whole lot more out there. People have been...
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
working hard for four to eight years or longer, they're in the 10 to whatever, 50,000. They're over the 10K mark a month. And so they've proven that there's a decent amount of value out there for it, for whatever they're building. But they're not so big that we have to go out and get millions of dollars to acquire it and stuff like that.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And they're just looking for liquidity and to move on to something else. It's hard. You guys have been doing it forever. So props on that front. But I'm like, it's really hard to do the same thing for a long time. So that's kind of my theory. And even after announcing Fireside and being at Railsworld, I feel like I had three or four people come up to me who were like, I'm in that boat right now.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
which is really interesting. So I think we're going to let the dust settle on this one and see if we actually are any good at this. I feel like we will be, but yeah, that's kind of how it, how it kind of came about, I guess is the thesis came from, look, we know rails, we know standardizing things across multiple apps. Cause I've never done one thing.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I've always had three things at a time and then I get too busy and I think, Oh, I should get rid of one of them. And so I get rid of one of them and then I fill it with another one. So I finally accepted. That's just me. I'm just going to have three things.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
yeah exactly yep i'm i'm kind of almost back in speaker deck as well again so it's like that's the in and out for the fourth time or whatever so how do you get back in on speaker deck where so my what where is in well uh equity sorry just equity so like my friend ownership yeah so my friend i sold it to my friend and so he's been running it and then every so often i come in and i help on it because it's a you know it gets a lot of traffic and a lot of scale so not just anyone can work on it people can work on it and build things but eventually it's going to struggle
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
I've got a lot of experience from GitHub, from words of friends, things like that in the past of large scale Rails apps. And so I'm able to come in and a week or two and kind of fix things up. And I was like, why don't we just come up with something? You can pay me if you want, or I can just maybe we can just hammer out some kind of equity thing.
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
And then Fireside dropped in and we're like, OK, let's figure out Fireside first. And he is also in on fireside. He's one of the people that joined on that. So, and he'll be doing the marketing and stuff. And so that's where it was kind of like, okay, like let's figure this one out first and then we'll figure out the other one after that. You built words with friends. Is that what you said?
The Changelog: Software Development, Open Source
The Moneyball approach (Interview)
So I didn't, I built, I scale, help scale it. So when I started, it was maybe, I don't remember like 60, 70,000 requests a minute and it was going down every night. And then I had some friends who were working on it. And one, one friend in particular, Jesse Newland. And he was like, I think, you know, noon's can help us. And so I was like, sure, I'll try.