Brian Casel: [00:00:00] Hey, it's Open Threads. I'm Brian Casel. It's my podcast. Welcome to it today. I'm talking to my friend, Ben Orenstein. He is the co founder of Tuple. app. He's also the co host of the Art of Product podcast. One of my personal favorites. I highly recommend it. It's one of those bootstrapper podcasts where he shares, you know, behind the scenes week to week.

Along with Derek Reimer on, uh, on what they're working on. So, you know, you'll get a lot of the story of what's going on with this product, um, over there in real time,

So many people on, on Twitter and podcasts and this industry probably know who Ben is, uh, I wanted to do one of these episodes where we hear a little bit more about what most people don't know about, about Ben and like the backstory of where he came from.

Um, he and I, uh. Come from similar parts of the world, northeast of the United States. [00:01:00] And we also both have a musical background. So it's kind of cool to like hear where he came from and how he sort of navigated. From the early days through college into after college, early career moves and how he progressed through thought bot and then finally onto his own and being an entrepreneur and running tuple.

So really interesting journey. I learned more about, about Ben's story here. I think you will too. A lot of really good insights and interesting bits of information. I just love hearing about these sorts of journeys. So it was a good one. let's talk to Ben. How are you doing? How's it going?

Ben Orenstein: Good to see you. Yeah, good to see you. I just thought I'd hang out in person with you and the microphone

Brian Casel: off a couple of weeks ago. That was fun.

Yeah, that was awesome. You're one of the several people I'm friends with on the internet and then met in real life several times and like, still every time I hang out with you in person, it's like, damn, I forgot how tall Ben is. It's like, you know, it's like everyone I know is either like way taller or shorter than I imagine they are on Twitter.[00:02:00]

Ben Orenstein: That is the thing I get consistently. I honestly thought about putting that in my dating app or my dating app profile. No matter what I tell you, you're still going to be surprised by how tall I am in person. It's just always happens.

Brian Casel: I'm probably on the other end of that. I'm probably like shorter than most people.

So people obviously know you from art of product and your work on tuple. I definitely recommend art of product. I listened to it almost every episode. And so. I think for that reason, I don't want to go too much into your work on Tubal because you share so much of it publicly week to week over there.

What I'm more interested in and, and even just knowing you for a few years, I feel like there's. Some backstory to Ben Ornstein that I don't really know that I'm kind of curious about. So what I want to know is about, and you know, the other thing that you and I have in common, we're both from like the Northeast here.

So where did you grow up originally? Originally from the Boston area?

Ben Orenstein: Yeah, pretty much. I was born in Western Mass, lived there for a while. And moved to Colorado and North Carolina for sort of three or four year stints [00:03:00] as I was, when I was much younger, but mostly Massachusetts. So I'm, I'm more or less, uh, I'm asshole.

Brian Casel: Right, right on. So what were you doing? Like as, as a kid, like what does young Ben Orenstein look like? Is it like, are you into sports, into music, into computers back then?

Ben Orenstein: Like what's that? Yeah. Played a lot of soccer. Wasn't amazing at it. Was not like a gifted athlete. I would say did a lot of singing, which I think we want to touch on later.

But it started at a very early age. I grew up in like a musical household, so there was just like singing happened all the time and like acapella Christmas carols and things like that. So music was a big thing from a pretty early age. Brothers, sisters. Yep. I have a younger brother. He does sales for a software company.

So we're kind of in a similar business now. It's the family age difference. Three and a half years. My dad was also in sales in the high tech industry. He worked for AMD, the chip makers for most of his career. And so that was actually really nice because he was in the tech industry. I got into computers at a young age.

Like we had a computer at our [00:04:00] house before a lot of people did, I think. And I discovered at a quite early age that I was obsessed with this particular thing and wanted to play with it all the time.

Brian Casel: That's cool. Yeah. I mean, my dad wasn't in the tech industry, but he was sort of like, One of like the early adopters of computers getting really excited about it.

Ben Orenstein: So like the old school like prodigy service. Oh, yeah Yeah. Yeah, I forget sometimes that that was lucky like I had a lucky break there I was exposed to this thing early on and the thing that I like fell in love with actually turned out to be like a Legitimate career. Yeah, it wasn't like French poetry that I got really into or something

Brian Casel: Totally I want to hear more about that in just a bit, but It's about, you know, I have a younger brother too.

He's about two years younger than me and we've been super close, like our whole lives, but the, you said your brother's in software sales. Mine is a farmer. Wow. Like he literally has like 40 cows and they produce milk and yogurt and cheese. It's like, wow. We're like, we couldn't be more different in, [00:05:00] in what we're doing as careers. It's just,

Ben Orenstein: did he stay in like the Northeast?

Brian Casel: Yeah, his farm is in, uh, northern Connecticut. Okay.

Ben Orenstein: Northwest Connecticut. Yeah. Do you ever feel weird, like, that you just, like, you don't actually make anything? Like, anything tangible?

Brian Casel: Sometimes. I never really had the yearning for, like, physical product. But yeah, like, when I think about what he's doing every day He's like up at three in the morning, milking cows.

It's crazy.

Ben Orenstein: Yeah. I don't think I want to do that.

Brian Casel: Yeah. Anyway. So music is kind of a big deal for you. Yeah. I definitely want to do a deep dive in music a little bit later on. You played some soccer, had some early exposure to tech stuff. Where'd you end up going to school or after high school? What did that look like?

Ben Orenstein: Yeah, I went to university of Massachusetts at Amherst.

Brian Casel: Okay. I remember visiting there. Right. I don't think I applied there, but it was one of them. One of the Northeast schools. I feel like everyone in the Northeast at least has to have that on like a list or a lot of people do,

Ben Orenstein: you know, it's kind of funny actually, it was not really on my list. It was my like backup and I was like sort of into these like more engineering focused schools or like [00:06:00] music focused schools like Ithaca or Union College or things like that. And so I got into a few of these places and I went to visit them and they were like all these like already back then, even like really expensive private colleges.

And I remember thinking I was like, okay, I'm gonna decide between, you know, one of these obviously. And my dad was like, You have to go see UMass, and I was like, okay, but I think I want to go to one of these. You have to go see it. And by the way, if you go to UMass, I'll pay for everything. But if you go to one of these private schools, you're going to take out loans.

And I was like, okay. And that didn't really mean much to me at the time. Cause I didn't really have a conception of what that difference really would look like. But knowing now solid.

Brian Casel: Yeah, sure. One of the things I always sort of regret is I ended up going to school in the Midwest, Indiana University and then Columbia College in Chicago.

But I, I always sort of regret like not choosing one of those Northeast schools because like I just really didn't stay in touch with any of my friends from college after college. And [00:07:00] most of it was travel really. And we had the internet, but it wasn't like it is today where it's so remote and easy to stay in touch.

Like traveling and distance was a much bigger deal around like 2000, 2003, 2004.

Ben Orenstein: Well, for what it's worth, I went to school, you know, an hour and a half from where I live now. And I'm friends with, I think one person from those days. So right. And it's a great relationship. He's awesome. But yeah, might not have been that much different.

Brian Casel: Yeah, I'm much closer still today with like my group of friends from high school. We've all sort of stayed in touch. So, I mean, I guess still, like, you know, young Ben, Ben Orenstein, I'm wondering, because I think about this sometimes, like the stupid question of like, like, what did you want to be when you grow up when you were starting to think about that as a kid, right?

Ben Orenstein: Mm hmm. Honestly, it was something in computers pretty fast. It was. Yeah. Once I, like, really discovered computers and dove into them, it was kind of like, what can I do? That's this. How is this? [00:08:00] And so I think so.

Brian Casel: What about like entrepreneurship? Were you thinking like I'm into software, but you were not thinking like products or business?

Ben Orenstein: No, no, no, not yet. In the beginning, it was just like, I want to program computers. I want to do this all day long. And it was like, I didn't really have a conception of like it versus like programming or whatever. I just like knew like computers, these are cool. I want to do these. And then as I got a little bit older and was in like high school, I think I like was in like computer science seems to be the major, I assume that's what I'm going to do.

That's what you ended up majoring in.

Brian Casel: You know, that's another regret that I think about is like, you know, now that I'm, I am in software, like as a basically self taught developer with the help of a lot of other stuff, but like having that, that CS degree, I feel like would have given me a lot more underpinning of everything that I ended up, I feel like I learned a lot by doing and figuring out and learning during the career, but I think about these like career software, people who have that understanding of how computers work from the inside out.

Ben Orenstein: Really could have helped. [00:09:00] I'd push back on that a little bit. A lot of a computer science degree, at least when I was doing it was like, well, first of all, you need to take a ton of math. Like I took, you know, like three calculus classes and linear algebra classes and all these things. And it was like, okay, I guess that's kind of like linear algebra.

I guess if you want to do machine learning, that's useful. Otherwise, not that much, maybe, or like graphics programming or something, a ton of math, none of which I find relevant today. Thank you. Some theory courses which may be interesting like the theory of computations like what is like a state machine And how do you make what are the fundamental essences of a computer which are kind of interesting?

but it's a little bit like it's a little bit like you want to be a racecar driver and I make you take a ton of classes on like Combustion engines and you know learn all the equations for how a piston works and it's like yeah that kind of helps But kind of not really

Brian Casel: Well, I see like I got into it From the standpoint of a designer and products first, and then kind of working backwards from like, what do I need to know or figure out in order to make a product on the internet?

Right? Yep. And that's [00:10:00] super useful, like practically to be able to like, basically ship features and ship products, but. I do find when I'm like planning features and architecting them and scoping out features for me and my developers, like I do feel like limited in terms of like, man, if I had the experience of working from the inside out, this would be a lot easier or more efficient, you know?

Ben Orenstein: That's true. I don't really think you, you probably can't get that in the class. My sense is there's a certain amount of wisdom to programming where you kind of have to just do it a bunch and be like, Oh, I've been burned by this and not by this. And like, you kind of have to see how decisions work out over time.

And my program in particular was not that they were not teaching that wisdom. Yeah. It was. Yeah. So it's. Computer science was kind of like an accidental beneficiary of the popularity of computers, where it was never really meant to be a, like, here's how you make great products, or even here's how you be a good programmer.

It was just the best fit that was already in an accredited program where there was a curriculum and everything. And it never has been really the best path, I think, if you want to make products.

Brian Casel: Yeah. But I mean, I'm also [00:11:00] kind of wondering about just computer science in general, where it's like, It's that classic thing of like, if you study it in school, like how far behind the times is it in terms of real world industry, right?

There must be some level of CS that is just, this is science. This is fundamentals, right? It's, it's always going to apply. Languages come and go trends, come and go framework, come and go. Like, what do you think that's looking like today for anyone listening? Who's sort of college age thinking about computer science.

Ben Orenstein: College is really fun. I think you should probably go. There's not a lot of times where you're going to get to do what you get to do in college and it's an amazing life experience and so you should probably do it from that perspective. Try not to go into a ton of debt to do it because it's probably not worth that unless you're in a, I mean, if you're majoring in computer science, you can probably pay off your loans to probably be successful there.

But I think you should mostly, like, my opinion of college is like, it's mostly a boondoggle financed by your parents slash the government. So you should like go have that incredible experience because it is really fun and like living by yourself for [00:12:00] the first time. It's great. So I think there's a lot of lessons and like enjoyment to be had there.

But if you're not that into that idea, you're just like I want to know how to like make things like I would say like a computer science degree is probably the slowest path to that. And like a bootcamp isn't gonna be a much better choice for you.

Brian Casel: For sure. I agree with that. Okay, so coming out of school.

Where are you going? Like, what's your first step out of school in terms of like, all right, got to figure out the whole career thing.

Ben Orenstein: Well, so maybe I gave a clue to it and describing college is fun more than anything else, but I was not a good student. I went into college kind of lacking self discipline and study skills and such and computer science was like too hard to sort of fake my way through or half as my way through.

So right at the end of my junior year, GPA fell low enough that they kicked me out.

Brian Casel: No shit, dude, I never would have guessed this about you for real, like I, I really always assumed that you, because I don't know, this is sort of like the vibe that you put off and like how you go about your work today and stuff like you seem super [00:13:00] disciplined and you seem like super like kind of on top of it.

Ben Orenstein: I appreciate that. And I think I mostly am today. I'm a very different person than I was at 18. Yeah, fortunately. So I'm glad to hear that. I was not that way before. I'm glad I figured it out. But honestly, I think it was actually that experience of getting kicked out of school. I felt very ashamed. And it was like quite a wake up where it was like, this is not how I want my life to go.

Like after I got kicked out, I got the first job I could find like as quickly as possible, which was bartender at the Olive Garden. And I was like, Just hate in life basically live with my parents tending bar in the mall Yeah, it was like this is not quite what I wanted, but it was good for me I'd sort of lived my life up to that point had to kind of been without consequence in a way like I lived like a Very sheltered life and had always kind of gotten away with all of the shenanigans I was pulling and this is the first time it really came home for real And I was like, Oh, okay, this is what consequences are like.

And this is all my fault. And I'm gonna have to [00:14:00] change if I don't want this to keep going on.

Brian Casel: Yeah. I remember I was waiting like right after or a year or two after college. I was living at my parents house, my dad's house, waiting tables at California pizza kitchen at the mall.

Ben Orenstein: Another chain. Yes. Yeah, man.

You had a name tag got non slip.

Brian Casel: Yeah. I had like the same, like a white shirt and tie that I wore like five times a week with all this shit all over it. And yeah, yeah, yeah. Like memorizing the menu, like inside and out every ingredient is like, Oh my God. And then dealing with all these people, customers, yeah, not fun.

Not the kind of customer support experience that I'd. Actually want to have, but I guess looking back, it was probably a good, I didn't have a good time, but it was probably good for me to go through that.

Ben Orenstein: Yep. That's how I feel about it as well. So I started clawing my way out of that hole that I had dug.

So I eventually, after maybe three months from that, I like found an it consulting gig where I was like a drive around Boston and like spend a half day [00:15:00] at like various client sites, like installing patches on their windows servers. And like helping people find the email they deleted and stuff like that, working for this like little small IT consulting firm.

And that was like a nice upgrade because at least I was in tech. You know, I was like, yeah, I was doing tech stuff. And what year was this? It's probably 2006 or so. Yeah, 2005, 2006. Well, only 16 years ago. How about that?

Brian Casel: And we're around the same age. That's around. I think I graduated in oh, oh, four.

Ben Orenstein: I was supposed to, I would have graduated in 2005 if I had.

Brian Casel: Yeah, very cool. So, I mean, I met you, I think, when you were at ThoughtBot. What was like the path from, from there into working at ThoughtBot?

Ben Orenstein: Yeah, so from Olive Garden to IT Consulting, and then from IT Consulting, I did a brief stint in sales at that place, like trying to sell the consulting services. It didn't go that well.

And then I got an entry level programming job. at this place called Metatech that makes hospital software, hospital suites, like suites of hospital software. And that was [00:16:00] great because now I was working as a programmer in tech, but the environment there was like crazy, like they had like the crazy like not invented here syndrome and like we're using all these weird proprietary technologies, so I really was not building up any sort of useful transferable skills.

So I was still kind of like very unhappy with my career outcome. For Metatech, I landed a Rails job, which is the first time I was suddenly working like a real. A language that more people used in a framework that was growing in popularity. I kind of like was starting to catch on to Rails, which was taking off.

This is like rails, like 2. 3 days or something like pretty early on. And that was really useful because I did a ton of pair programming with a more experienced person and got me up to speed, like taught me actually had to be a software developer. I taught me the engineering practices.

Brian Casel: Yeah. That's pretty later on.

Ben Orenstein: Yeah. Right. Exactly. Yeah. That was very formative and showed me the, like the engineering practices, you know, it was like, how do you actually make software beyond just like knowing how to write Ruby? How does a team actually make a product and keep it going and update it and deploy [00:17:00] it?

Brian Casel: I think back a lot to my first real job, like after the waiting tables, I started as an intern and then an employee at a web design agency in New York.

And I had hacked around with HTML and CSS before that, but. That I remember telling the person who hired me, I want to go from like amateur to professional at designing and building websites. And I was there for about three years and I, I don't think I would call it pair programming, but I physically sat next to a person who just mentored the hell out of me in terms of like, here's how CSS really works.

You know, he was a few years older than me. If you were more experienced, just so incredibly valuable, like literally sitting next to him and. Feeling terrible about bugging him every five minutes when I run into a hitch, but like he was so nice about showing me how things work. And then the other thing that I remember about those years was my manager who would task me with these little projects like, okay, we need you to build this navigation menu on Coca Cola's website, right?

[00:18:00] Massive visible website and stuff. And I don't know what I'm doing. She was like, you got to figure out how to do this crazy design that the designers came up with. It exists over on that other website. Pepsi does it. So it must be possible. Go figure out how to do it. Like the source code on undo it and figure it out.

And like, that was such a valuable skillset to learn. And like, I was so frustrated going through it, but like, then you just get better and better about figuring out how to build something that somebody else has built.

So you're getting started with rails where it's like, in terms of like workflows or skill sets that unlocked superpowers that, that lasted the rest of your career. Like for me, that's one of them. It's like the ability to like figure out how to build something.

Ben Orenstein: You know, it's hard to break it. down. I mean, I learned so many, I feel like I basically went from because it's like I touched on, there really was not that much programming in my computer science degree.

There was some, but not a lot. I was doing some programming at Meditech, but not like. [00:19:00] Not any sort of modern programming. And so when I joined this place, it's called Dana Farber. It's a cancer research Institute. When I joined Dana Farber, I was actually writing Ruby in a rails app next to somebody kind of all day long.

And we would like pair program, like, like I would plug a keyboard into his computer and we would sit next to each other and we would like tackle things together and he would review all my pull requests and gave me a ton of feedback and being right next to a. Person that cared a lot about the craft of programming and knew a lot about it was really what actually turned me into a like a software engineer, like someone who could make something happen for real, because there's like 5000 things around programming that are involved to like actually like get a product out the door.

And so it's not just like, do you understand ruby syntax? Do you know what the object hierarchy looks like? It's like, yeah, sure. That's part of it. But there's like a million other things along that goes with it. This is around when I started learning Vim, for example, which became like a pretty core part of my toolkit.

I'm still a Vim user today, like years later, more than a decade later. [00:20:00]

Brian Casel: So, all right, ThoughtBot. That's when I first, that came next in the timeline for you. So like, for those who don't know, I mean, ThoughtBot is a really well known Ruby on Rails consultancy, right? They work on pretty huge. Mostly client projects.

They have some products of their own, right? And then they run several pretty big open source gems and whatnot for the rails ecosystem. How did you get in there? What was your path like within ThoughtBot?

Ben Orenstein: The ThoughtBot headquarters was in Boston and I was living outside Boston. And I, I met one of the partners at a Boston Ruby meetup, Dan Croak, who was sort of like the, he eventually became the CMO there.

He was like the pretty actually kind of official ambassador of ThoughtBot into the world. Kind of a born keeper in touch sort of person, like a really great networker in that sense. And so he and I met up at the Ruby meetup and we stayed in touch. And then I think the next major thing was that there was the rails rumble where people were, which is like a hackathon over the weekend.

And I think I ended up, he [00:21:00] invited me to his team, which had him and a couple other thought potters on it. I got to do a rails project with him and that was super useful for all the, you know, networking reasons you might assume. And somewhere after that, I believe They decided to hire some more people and he sent me an email and said, Hey, we're hiring people.

Are you interested? You're my first email. Are you interested? And I had some doubts, you know, at the time I was like, thought about it's like if they're like the top, like there's no way I'm going to be able to like, I remember the thing that I was most worried about was because it was client like high hourly rate client work.

I remember feeling like there's no way I'm going to be able to like produce enough work that the clients are going to feel like they're getting value for this money. Like, I don't think I can work that hard for that long. Like, I was worried about, like, my ability to, like, work enough to justify our, our consulting rates.

But I unfortunately had a friend, actually the friend from college, the one that has remained, he, like, just, like, refused to hear that. He was like, no, no, no, you're doing this, you're trying it, you get in there and give it a shot. Don't be an idiot.

Brian Casel: I mean, that sounds like it's a, kind of like a step up in your career, right?

Yeah, for sure. So, Yeah, like [00:22:00] networking wise, I'm assuming like salary wise, right? Like getting a bump up. Yeah. And then you were there for several years, right?

Ben Orenstein: Yeah. I mean, so Thoughtbot was a huge shift in the curve for me. So part of it was that I was learning even more about how to be a good programmer.

Like we used to have these weekly dev discussions. And like the CTO of ThoughtBot, Joe Farris, would like just come in with a topic and like teach us things and he was like, unbelievable, he's the best programmer I've ever met still. So I got to kind of like copy a lot of stuff out of his brain and into mine.

ThoughtBot cares a lot about code quality. And so there's such a strong culture of just like producing really good codes. There's a ton of people who want to help you with this and have strong opinions and will kind of contribute to your learning in there. And I was super into it at the time, so I was just soaking it up as much as possible.

So another major thing happened during my ThoughtBot time, which is that I went from, originally I was a consultant at the company. I was writing Ruby code for clients, just like everybody else. At some point I got the bug to try to make a digital product. And so peep code was this, the series of screencasts that were really popular at the time, like really [00:23:00] highly produced screencasts on technical topics, including stuff in the Ruby world.

And he put out the screencast of like how to make screencasts. And I was like, I was like, got it and watched it. And I was like, I can do this. And so I decided to make a screencast about, and the title was Vim for Rails Developers. It's about all these like, you know, like sort of like workflow hacks and stuff that I had put together and learned.

And I made a screencast and I put it up for sale for nine bucks and it started selling. And that was kind of like my introduction to like, Oh my God, you can make money on the internet and it's amazing.

Brian Casel: Yeah. And that was your personal product and

Ben Orenstein: Personal product. First. Yeah, exactly. I did it on the weekend.

Actually, that was slightly dated. Predated thought. But now that I think about that, mixing the time in Thailand up a little bit, but yeah, that was before that, but I had this taste where I was like, this is amazing. I want this.

Brian Casel: Yeah. There's nothing like that. Very first selling something digital to a stranger on the internet.

Ben Orenstein: Unbelievable. My heart started pounding the first time I like got my first sale notification. I couldn't believe it. Yeah, I felt like I was like, I was just like on drugs.

Brian Casel: I totally remember that too. Like I was telling web design services for thousands [00:24:00] of dollars. But then I sold a WordPress theme for 49 and it was like, Oh my God, like, I can't believe it.

Ben Orenstein: Yeah. There's nothing like the email that says you got money and you don't have to do anything in like four. It's already there. There's no more follow up. It's done. Like, that's just like, Oh my God.

Brian Casel: When did the podcast, because your first podcast and stuff was through Thoughtbot.

Ben Orenstein: Correct. Okay. Yeah. So some major things happened at ThoughtBot.

So one was I started a podcast, actually they encouraged me to start hosting their podcast. So it's called Giant Robots Smashing into Other Giant Robots. And the CEO, Chad, there said he thought that I would do a good job hosting it and that they would handle all the production. And I was like, okay, I'll try it.

And so I started off as an interview show, which ended up being amazing for my career because I just got to interview all the major personalities of the industry like ThoughtBot was, is and was well known. And so it was like, I want to come on the ThoughtBot podcast. Yeah, sure. So I was interviewing DHH and a bunch of other realist core contributors and kind of anybody interesting in the open source world and other [00:25:00] business owners within the space.

So that, that was just great and super useful. And then also I discovered that I loved giving conference talks. So they had a, like a reimbursement program where they would cover all your expenses if you were speaking at a conference. So I just started applying like crazy and it was partly, honestly, I want to do some traveling on the thought bot credit card.

That's like, well, yeah, there's a Ruby conference in Australia. Uh, I need to fly to Australia and give this talk.

Brian Casel: Of everyone that I know who everyone comes from some previous gig before you go out on your own. But like, you know, you really had like one of the most optimal, like optimized, like pre entrepreneurship career building blocks in there.

I mean, not ThoughtBot, but Get really, frankly, just building an audience for yourself, even though it was, you're from Thought Bot, right?

Ben Orenstein: Totally. Yes. It was a big win win. Like I would go on stage and like, I'm Ben Orenstein. was getting good impressions of it, but also I was getting 50 to a hundred Twitter followers every time I gave a talk or more.

And often they [00:26:00] would get, you know, recorded and put on YouTube and pointed back at me and I was just steadily building up this group of people who thought I knew what was up because I was doing a good job on talks.

Brian Casel: Yeah, pretty sweet. So, I mean, I did want to sort of like navigate to your decision to leave and go out on your own and then eventually get into Tupel, but what I'm kind of curious about, correct me if I'm wrong, but like, again, like you have this sort of amazing role at ThoughtBot you had.

Right. And I mean, like, did that make it difficult to make the decision like that, that you do want to leave? Or was it something that you were always. Planning on and aiming your trajectory like eventually I'm gonna I'm definitely gonna go out on my own or was it like a man? This is a cushy job here really works out.

Well, like was it a

Ben Orenstein: yeah So there's one other major thing that happened at Thoughtbot that I think sort of leads into the answers to those questions Which is my screencast was still selling and I found myself wanting to make more and also I was having a lot of success giving Talks and workshops and [00:27:00] things like that and Thoughtbot was also putting on like the expensive in person workshops and such And one day I went to Chad, the CEO and said, I think we should take all of our all the content I've made and the content of thought has made and we should put it behind a subscription and we should sell it to people to build a community around it.

There's a lot of people that want the knowledge that's inside this company. And we should make an educational business. And to his credit, Chad was like, yeah, I agree. Go ahead. That was a big thing at ThoughtBot. That's like probably one of their biggest strengths. I feel like it was just like you want to start a thing, like start the thing, like don't even ask about it.

Brian Casel: That's a great idea. It's a great idea for you to go do.

Ben Orenstein: Yeah, exactly. You want to do it? Do it. Yeah. And that was a really strong vibe there. And that was I think really a strength of ThoughtBot's culture and Chad's management style. Yeah. So I did. And we spun up this business unit inside the company and we called it Upcase.

And We started making more and more courses. We created like a weekly, uh, shorter kind of tips video, a lot of significant educational material altogether and made it like a recurring revenue business. And so I got to practice building like an [00:28:00] educational subscription SAS more or less, and that got to be pretty large.

I think it was 30 K a month or something at its peak. Like it was a pretty decent size business. It was never quite as good as the consulting business, but it was real. It was like my first, like, Hey, I'm making a thing from scratch and like it has revenue and users and I'm making decisions about it. And that taste of that was like, ah, yes, this is where I want to be.

Like the intersection of like code and money and subscriptions was like, oh yes, this is even better than info products. So

Brian Casel: I mean, from there, like what was the actual sequence of events where you were like, okay, like this is the year where I think I'm going to go out on my own. Or, you know, I sort of remember the early days of tuple.

And I remember you were sort of dabbling with a couple other, there was like a podcasting product in there. And like, Product wise and like, in terms of like your next chapter, were you starting to, I know you partnered up with Spencer and Joel, like, was all that like happening while you were still employed at ThoughtBot or was it like [00:29:00] go out on your own and that came together afterward?

Ben Orenstein: Yeah, no, I, so I was at ThoughtBot for seven years. And that to me for a single job is like crazy. Like that was like a hell of a tenure, I think, especially in tech. So I was like overall so happy there and it was very cushy, or like I had been very happy there and it had been a wonderful experience. But eventually I sort of looked around and thought like, I don't really know what's next for me, but I don't really see the next step here.

I think I need to go out on my own for the next thing. And I didn't really know what I wanted to do on my own, but I knew I wanted to take a crack at it rather than like waiting around. And actually this was kind of, as I was deciding this, I had a call with Rob Walling and was like, here's how much I've got saved.

Here are some of the ideas I'm thinking of doing. Am I crazy to quit my job? And he was like, nah, you're fine. Go for it. It's like, you're a good teacher. You could make educational products. I would encourage you to try that. SAS is hard, but maybe try that someday if you want to, you got some programming chops.

So maybe you could start that earlier than most people, but he didn't think it was very risky. And I [00:30:00] pulled the trigger and left.

Brian Casel: So like savings wise, you felt like you had enough time. To, to figure something out.

Ben Orenstein: Yeah, I think I had something like 10 months of savings, so a reasonable burn rate somewhere around there.

Right on.

Brian Casel: And then, you know, like, I'm not going to get into the whole, like story with Tupel and everything, but I am just curious about the very earliest days to kind of round out this whole segment here, like how you got from young Ben Arnstein to here. You know, what I sort of remember about the early days of just tuple as a product is a very complex thing to build from the ground up.

Right. And it was a really, I think it was like what, like over a year of just building before it could be used

Ben Orenstein: About nine months from breaking down to having our alpha.

Brian Casel: Got it. So what was that time period like in terms of like, okay, we're building this thing. We think there's a market opportunity here, but you don't really have like first customers.

Maybe you had like early commitments, but not a business yet. Right. So what was going on for you around that time?

Ben Orenstein: I would [00:31:00] say my dominant feeling was cautious optimism. I was having success selling the idea of the product to people. People were paying us for early access ahead of time, like thousands of dollars.

And when I told people about the idea, they seemed excited. And it seemed like, okay, when I sell this dream, people want the dream. They want to buy it. And the question was just like, can we deliver on the dream? Like, will we make something that is like close to what we're describing? And for a while, the answer was like, don't know.

And it was, it was kind of always like, it started off like no idea and like it slowly turned from no idea to like, maybe like possibly, and with moments of, Oh my God, definitely not. Never were. Oh my gosh. I actually remember an early, like, I think I did an alpha call with you one day, I had like a journal entry, like you and I tried to use the product and it was just like a total disaster.

And I was like, Oh my God, we're never going to launch this thing. You were on some weird connection where you had like almost no upload bandwidth. So the call was just like total trash.

Brian Casel: I've since upgraded my connection since then, but I sort of [00:32:00] remember even where I live now, like, we, like, we don't get, you know, fiber here, whatever the highest cable offering is same.

Ben Orenstein: Yeah. Still not that high. Yeah. So that was actually like, that was supposed to be a few weeks before we were like, hoping to launch. And like, I tested it with you and it was like, oh my God, we are so far from ready. But fortunately the actual real problem was your upload bandwidth was terrible. Yeah, exactly.

Yeah. So you gave me a scare there.

Brian Casel: What's I think kind of funny is that Gary, you were saying like earlier, you know, you started in software, you were always interested in software. You went into software schooling wise and career wise, you had a stint in sales that didn't go so well. And now when I think about your role in tuple, you're the sales guy, right?

At least you were for the first few years of it, right? Yes, your partners are more on the technical side and yeah, I think it's interesting how you've taken on that role of like you made the first sales. You helped you talk to customers.

Ben Orenstein: Yeah, it made sense to have me kind of be the face of the company because I had, I came to it with a big audience, which was just so useful.[00:33:00]

And so I would say I am still to a decent extent the face of the company, like I'm the one doing podcasts like these, although the team is growing and like there's more of our team members out there doing stuff like and reflecting back at the company, which is like a really cool transition to have happen.

But I would actually say my focus these days, I hired someone to handle sales like a head of sales. And so my focus mostly now is product like hiring when we need to. Fortunately, we're paused and hiring for now because we have the team we want for the moment. Um, and then product, which has been great.

Like my day to day was writing up a shaped pitch for the next feature we're building. Yeah, very cool.

Brian Casel: All right. Let's shift gears here a little bit. Okay. We're going to wrap up this segment. Well, thank you, Ben. And it's always a great time to chat with you and yeah, we'll keep it going.

Ben Orenstein: Sounds good.