Software Developers Journey Podcast

#51 Ben Orenstein advises us not to worry too much


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Tim Bourguignon 0:06
Hello, and welcome to developer's journey. The podcast shining a light on developers lives from all over the world. My name is Tim Bourguignon, and today I received Baron orange Stein. Ben spent the last years working at football in Boston, where he and his colleagues obsessed about code quality, and keeping shipping speed high. You might remember a thought but from the last episode with Sarah neoteric. This is where Sarah on the apprenticeship. There, Ben co created the uppercase course one of many products that been created. Benny's, the author of the refactoring rails course the code quality challenge, trail mix and briefs products, we might talk about it during the podcast. And he's currently building tupple tool for remote pair programming. And thus, it is not surprising to hear that Ben is also the host of the art of product podcast. Ben, welcome to the afternoon. Thank you so much. I'm psyched to be here. I am psyched as well on site as well. Let's keep on this product journey. Where do you energy comes from for building so many products? This is insane.

Ben Orenstein 1:18
Hmm. I think maybe this like might be one of my superpowers, in that it doesn't feel like that much work. To me. There's something like I just love making a new thing. I'm kind of addicted to the first six months of any project, like I love getting things started. And like turning nothing into something. I'm admittedly less good at the next part, which is the like maintaining it and staying focused on it and not getting distracted by new thing. But the energy has always just been there naturally. I don't know where it comes from.

Tim Bourguignon 1:51
Okay, and how does this second part goes, then when you have a product rolling? And what happens then?

Ben Orenstein 1:58
Well, I'm kind of finding that out. Now, to be honest. So I'm working on a new company. We're about a year old now. And so we actually, I would still say we're in the early phases. So it's not quite, it's not quite happening yet. In the past, it's been hard for me to sustain interest. If I think my brain is wired, such that I'm very interested when it's not clear if something will work. And there's lots of things to be figured out. And then once I kind of feel like the big questions have been answered, and the rest is the left to do is to execute on those ideas around those sort of plans. And to keep it going, I think I lose a bit of interest. So we'll see how I do with Drupal, I think this will be more interesting than usual. Because I it's something that I I own a part of and have built from the ground up. So hopefully it won't be too much of an issue. We'll see.

Tim Bourguignon 2:55
Interesting. So the technical challenge is really triggering your brain. And then the organizational or marketing or whatever, is not that much of your cup of tea.

Ben Orenstein 3:07
Did I get that? Right?

Ben Orenstein 3:09
I'm not not quite actually I don't mind sales and marketing. That's actually mostly what I'm doing for tuple. I have two other co founders. They're both technical. So there's plenty of people to write code. So I'm focusing mostly on sales and marketing. And I'm enjoying it quite a bit I bit actually it's it's fun. It's more, it's less about the kind of work and just more about the phase of the project. I think we're I'm really good in the figuring things out phase, and then less good in the stay focused on this and keep paying attention and actually push this thing all the way over the finish line phase, I would say

Tim Bourguignon 3:43
that's interesting. I think I've not really was product, but the same kind of leadership, I'm very interested in in getting people to move their ass and to start something. But when it becomes organizing, as well as less my stuff, like I kind of relate to what you're saying. That's That's very interesting. But you are still very technical and your journey started as a developer, right?

Ben Orenstein 4:09
Yes, that's right. Yeah, I've been programming for about 14 years now or so.

Tim Bourguignon 4:15
Okay. Would you like to take us back there?

Ben Orenstein 4:18
Yeah, sure, why not? So the first time I really actually did any programming, I was a senior in high school. So I ended up finishing high school a little bit early, I had enough credits, I'd taken enough classes that I didn't need to. I was ready to graduate a little bit early. And there was fortunately this program at my school where you could go take classes at a local college for free, instead of just kind of hanging out and waiting to graduate. So I went to a local university and took a computer science class, and it was like computing one on one. And it was there was a great professor named was Jim canning. And he ran this wonderful course where it was almost entirely at the beginning of the year. He gave Give us this stack of paper that described like 120 different little programs that you could write. And your grade was largely dependent on how many of those programs Did you get written before the course was over. And they started off very, very easy. And they got, you know, tricky towards the end. And so that was my first, like programming. exposure for real where I was really doing it in earnest. And turns out, I loved it, it was just so fun. I love the class, I love the assignments. I did well, in I did well in that class, which was actually sort of an anomaly for me, I have not historically been that great academically. And but this was sort of the first time something really caught my attention that I really loved it. And I really poured myself into it.

Tim Bourguignon 5:43
Interesting, and how did you go from there? Well,

Ben Orenstein 5:48
from there was a bit of a windy road, actually. So I had this good success early on, I was like, Oh, I love programming. This is fun. And so I enrolled in a whole bunch more computer science classes when I when I did go away to university. And it turns out, I had not developed that much maturity in high school. And I was not ready to for a full course load. And I did really poorly actually. So I ended up getting kicked out of college, towards the end of my junior year for not for my GPA falling below a certain threshold. And they're like, it triggered this automatic suspension, basically. So I had to leave the college for a while and kind of get my life together. So it was it was those sort of a, how do I get a good promising first start, whereas like, Oh, I love programming. This is fun. And then it's like, oh, actually, I, I haven't learned how to break down projects. And I'm a bad procrastinator, and I don't have a lot of maturity, honestly. So I had a bit of a setback early on.

Tim Bourguignon 6:45
But you seem to have gained a tricky system, right?

Ben Orenstein 6:48
I hope so. Yeah. So it turns out getting older. And you know, so this was kind of this is the first time in my life, I had really faced consequences for my actions, I lived a very idyllic childhood, it was pretty wonderful. And I had more or less just dodged responsibility for so long that I didn't really know how to deal with it. But finally, my bad behavior caught up to me. And so I moved home and was very ashamed and very sad. And I got a job as a bartender, and was really embarrassed. And it stirred something in me where I basically just stepped back and said, This is not how I want my life to go. And so I started applying for better jobs and started getting them. I had some IT skills from like an internship and playing around with computers as a younger person. And so I managed to get a job as like an IT consultant. And so I was now in the tech field, which was great. And sort of kept applying for bit like working somewhere for a little while and then applying for a better job and just kind of like stair stepping my way up through the professional world. Until eventually I was reading code full time as a developer, and actually still haven't still don't have a degree. And it's looking like it's probably not going to happen.

Tim Bourguignon 7:59
But not even apprenticeship.

Ben Orenstein 8:03
Heck, no degrees of any,

Tim Bourguignon 8:06
how did this this working up the chain work? Did you? Did you choose a language and stick to stick to it? Or did you go with the flow wherever you could find?

Ben Orenstein 8:17
That's a really good question. So there was a big turning point. So I managed to land a job as an entry level developer at a company. And that was a kind of it felt like a big win. At first I was like, Oh my god, I'm gonna get paid to write software. This is amazing. And they were they had a nice trait in that they hired entry level developers. So they gave me this sort of like, logic test and kind of like programming test. And I did really well on it. And they're like, Oh, you seem like a really good candidate. But I ended up kind of really hating the, the company culture there. There are some serious problems with it. And I was actually fairly miserable there. And so my performance on the job was really suffered. But I was excited enough about programming that I really wanted to find a better job, I knew that there were better jobs out there. And so I started teaching myself Ruby on the side. So I had bumped into Ruby, extremely early, actually, I bought a book on Ruby, I think in the in like 2005 maybe, which is really early on. And I was amazed by it because I had been programming C and then there was this thing called Ruby. And it's like, oh my god is like just like ridiculously higher level. It blew me away how like my only exposure had been to the programming world was in C where everything is very low level, lots of manual memory management and things like that. And suddenly, he was incredibly expressive language. So I had I had it piqued my interest, but I didn't think there was any way you could do anything with it because it was just this fun play language out of Japan. And then Ruby on Rails came along. So when I was at this job that I didn't like with a bad culture, I was teaching myself Ruby and really teaching myself rails on the side and I bought the Agile web development with rails book from pragmatic programmers, and I built a building like some little Rails apps on the side and Somehow, like a friend of a friend forward to the job requests a lot a job description my way, and was like, hey, like, there's this organization that's looking to hire an entry level rails developer. And I was like, Hey, I could be an entry level rails developer. And I applied and I got in. And this was night and day like that. It was it was a small team, that my boss was great. We pair programmed almost every day, he used vim. We got just like very willing to adopt new technologies, really supportive. And I basically was his apprentice, pairing almost full time for months, and just completely leveling up my development abilities. And that was really like a big turning point for me.

Tim Bourguignon 10:40
Fascinating. There's many questions I want to ask which one? Which one? Which one? Um, when let's go with this one. You were developing in see before and we talked about this, this producing something in a product. This is what I connect to my mind with Ruby on Rails is creating products is being very efficient at pushing something out the door. Is this something that you felt at that time?

Ben Orenstein 11:09

Ben Orenstein 11:12
I guess? No, at the time, no, I was just interested in is there a way I can write Ruby and get paid for it? Because I was using this, like proprietary language at the job I didn't like that you wouldn't even recognize the name of because they wrote it. And they only they were the only users of it in the world. And I was like, I hate this language is terrible. And then I was using Ruby on the side. And I think this is beautiful. And it's like, how do I get paid to write Ruby? And it's like, well, the only answer for that for a long time. And almost still, I would say is write a Rails app. And so I started learning that.

Tim Bourguignon 11:42
Okay, make sense? Make sense?

Ben Orenstein 11:45

Ben Orenstein 11:46
I didn't like once I'd later on I would discover how good Ruby like Rails is at shipping prototypes. And that was just sort of a side benefit.

Tim Bourguignon 11:55
Okay, yeah. Make sense? And how did this not apprenticeship, but you said you were you were kind of the apprentice of your former boss? How did this relationship evolve between the two of you?

Ben Orenstein 12:08
I think, well, so I was kind of fortunate in that there, there was, and probably still is a bit of a labor shortage for experienced rails developers. So at the time, there were no boot camps teaching you Ruby or rails. And so there's almost nobody with a lot of real experience in the world. And especially like, let alone in their geographic area. And so they tried to hire an experienced person, but everyone was trying to hire an experienced person, and then very few existed. And so they failed. And that job ad was up for months. And then they said, Okay, let's, let's try something different. Let's try to hire a junior person. And we'll just have to invest the time to train them up to speed. And so they were, they came into it fully aware that I was fairly new. And at this point, I had like, really like, I think I had basically successfully made one Rails app. And it was simple. And like, it talks to an Amazon service to talk to Mechanical Turk. And like, was, like, really, like, barely did anything. But you know, I had learned how to write some tests. And they really appreciated that because they had a strong testing culture. And I had shown some initiative, I had shown that I was willing to do this on my own. And they kind of took a bit of a risk on me. And so they, I started my first day, and they clearly knew, like, I didn't know that much. And so my boss just basically said, like, Look, I'm gonna, I'm gonna teach you things, I'm gonna get you up to speed. And so that's where I learned to like pair programming, and I just spent a lot of time sitting right next to him.

Tim Bourguignon 13:38
Do you have an idea why they choose you? You say there was a shortage of labor? But what what? Interested them in your, in your profile and your psyche? In your way of thinking?

Ben Orenstein 13:51
Hmm, I don't know. I mean, I might have been one of the only people to apply like this, this ad got passed through a friend of a friend and like it was being circulated around, I think, because they were having such a hard time filling the position. And they weren't paying that much at the time. Like it was way more than I had been making. So it felt great to me, but it wasn't like a super competitive salary. So I think is literally just like, no one else wanted the job. And I showed up and was eager. And, you know, seems smart enough in an interview that they said, Alright, let's, let's take this guy. Okay. So let's flip the question around

Tim Bourguignon 14:23
15 years down the line. So So now, if you were to, to pick a junior developer to, to keep under your wing and teach Ruby on Rails, which would you be searching for?

Ben Orenstein 14:35
Hmm, that's interesting question. Like, what kind of personality traits but I look for, is that what you want to know? Yes, yes. I guess the biggest one is something like grit. So the the ability to push forward and suffer a little bit and not get too discouraged. I think So much of programming is existing in this space where you don't quite know what to do. And you don't know why this thing isn't working. And it totally should work. And it doesn't. And you have to figure out why. And there's a bunch of different ways to figure out why. And but it's kind of it can often just takes a long time if you're just feeling stupid. And pushing through that discomfort. And something I often tell people is like, I tell junior developers in particular is that feeling doesn't go away. The problem is just get trickier. Like it takes more to trip you up. But you'll still spend tons of time as an experienced developer being like, why doesn't this work? This should totally work. And so I think that meta skill of like, just living with that discomfort, and not throwing your hands up and saying, well, doesn't work, whatever, I can't do this, I'm not smart enough, or, like, no one else is struggling this way, or something like that, is probably what I'll be looking for.

Tim Bourguignon 15:55
That's interesting. One of the guests that has not been published yet said pretty much exactly the same thing. You say that seniority is, is being how do you how did you put that being at ease with not feeling stupid, but kind of feeling stupid or feeling feeling uneasy with the tasks that you're at? And so so knowing that is it is normal process, and this was his definition for seniority, which I found very interesting. Yeah, I like that. Um, so what happened after these, this first apprenticeship in air quotes, in Ruby on Rails?

Ben Orenstein 16:37
Yeah, so. So that was a huge turning point. For me. I had gone from, again, to my previous job had been programming, but I really didn't like it, the culture was very bad. And then I went to a better job where I was still programming, but making way more money and a much better culture and loved it. But I felt like after a while, after about two years, I had kind of learned about as much as I was going to learn at that job. And I wanted to keep leveling up. My favorite, my favorite thing in life, I think, is just getting better at things. And so I started slowing that that progress started slowing down. And I they, there was like politics involved. So I couldn't really get promoted. And it was just like, looking like there was not much there to be had. So I started looking around. And along the way, I had become friends with someone over a thought bot. His name was Dan croak, who's like one of the best all time best networkers of all time. He's just amazing at meeting people, and sustaining friendships and staying in touch. And so he and I had been friends. And at one point, he like reached out to me, or I can't remember who reached out first. But we started a conversation and I was like, Alright, let's, let's get this ball rolling. And so I applied to thought bot, and, and got accepted. And that was a turning point number two. So like the, my rate of improvement had changed tremendously when I went to this first job. And then thought bot was like another like, I don't know, doubling or something of my ability. Because everyone a thought bot was more experienced and incredibly passionate, devoted to quality, and learning and sharing. And I was just like, steeped in this culture, that was just amazing. And this was, like, even an even bigger turning point for me, like, I couldn't have gotten a hot pot without the previous job, but thought, I think it's made everything else possible for me, because I learned how to like I learned how to really write good code there. I learned so much from the co workers there. And the culture, a thought bot is very much based around sharing, and teaching. And so because of that, I was encouraged all the time to make courses and give talks, and write blog posts and tweet useful things. And through doing that, I host a podcast that was actually where I began podcasting, I hosted the thought bot podcast for about five years. And through doing all that, which is something I was just having fun doing and enjoying and feeling good about giving back, I developed my own audience. And so there were there's, you know, over time and a larger number of people just following me and wanting to stay in touch with what I was doing, and wanting to learn stuff. And that has been what I feel like has kind of unlocked the next phase of my life, which is what I'm doing now working on tuple like, coming into tuple having that audience of Twitter followers and newsletter subscribers and YouTube subscribers and all that has been incredibly useful for my current company.

Tim Bourguignon 19:26
Let's, let's unpack this a bit. There were a lot of information there. Um, what does Flipboard do? Exactly? Can you summarize this for the for the audience, please?

Ben Orenstein 19:34
Yeah, so thought is a, I would say primarily Ruby on Rails consultancy. They may be that may be less true every year. That's, that's less Rails is happening and more other things. But when I joined it was about I think I was employee number 27 or something. We were under 30 at the time. And everyone was reading Ruby on Rails and for other companies. So we were like a consulting firm.

Tim Bourguignon 19:59
When you add your clients, or will you in use at both offices with your coworkers,

Ben Orenstein 20:07
almost always in the offices, and that was one of the core values early on. I think that's less true now. But early on, we strongly preferred not going to client offices. And so we would try to have clients come to us, or we would work like semi remotely and meet up with them. Once a week or so,

Tim Bourguignon 20:23
yeah, that makes the, um, the sharing among peers way easier, at least inside your Yeah.

Ben Orenstein 20:31
Right. And when you're, when you're working on with a client, you are not, you don't work there, you'd like you're an outsider. And so being in their office feels like being a guest in someone's home. And so it's can be pleasant enough, but you're not quite relaxed, versus being around your thought coworkers who you know, who you have known for years and thought bots, like very nice offices, it was just more pleasant.

Tim Bourguignon 20:51
And hunky. Do you deal with the pressure of producing something for the client and your standards for quality? matching those two?

Ben Orenstein 21:02
That's a secret question. So I almost didn't take the job. I almost never applied actually. Because I remember thinking like, okay, sapat bills, like something like $200 an hour. And there's no way I can get, I can produce stuff that's worth that. Like, if I'm building that much, I'll have to be working so hard that I probably can't sustain that level of output. And a friend of mine was like, No, no, shut up, just just apply anyway. And he was right, it was fine. But the the trade off of quality versus productivity is not quite so black and white, I would say. So I think it's like, if you're only ever going to ship one feature, you can write the feature really crappy. And like just like at the really simplest quick and dirty version, and ship it and it's fine, that will be fast. But if you have to write a new feature the next week, and another one in the next week, and then fix bugs the next week and the fix bugs the next week, you don't really gain that much by shipping the crappy version. So I think people think there's like this, this this trade off of like, it's either fast and crappy, or slow and good, like slow and high quality. But I would say actually, like, if you want to maintain a consistently fairly high speed, you have to have it be high quality, you can't actually really trade off quality and speed quite as easily as some people might think you could.

Tim Bourguignon 22:28
I absolutely agree. I've just lived the the flip side of this being at a client and having the client brief down your neck and kind of observe what you're doing and kind of have a say I'm micromanaging what you're doing and have a say in which quality measures come in and don't come in. That's why I'm asking this this question. I guess if you're if you're remotely and the client doesn't have a complete oversight on of what you're doing, then it definitely makes sense to to shoot for quite a year. Yeah,

Ben Orenstein 23:03
I would say that even if we were in the clients offices thought it was very good at only taking clients that were willing to defer to our judgment as to how something should be written. So we we didn't work with micromanaging clients. So we would sort of fire them as customers if it if it turned out that that's what they wanted to do. There were times where they would say, look, this is super high priority. We need this shipped by whatever. And then so sometimes we would, you know, do the faster version perhaps. But for the most part, we would hire customers that gave us plenty of notice that we knew deadlines well in advance so we could plan so we could cut scope as needed rather than sacrificing quality.

Tim Bourguignon 23:45
Makes sense is a good position to be in. That's cool. Let's unpack some more. You said you started making courses and then holding talks. That's right.

Ben Orenstein 23:58
That's right. Yeah. I've always really enjoyed teaching. There's something about taking a complicated topic and finding a way to explain it clearly. And sequencing that knowledge so that I teach you like what you need to know at that point. But not so much that you get overwhelmed, I just think is a really interesting challenge and requires kind of empathy, and an analytical nature and an understanding of humans. And that the combination of the skills I find is really intriguing and a fun challenge. So I had always enjoyed teaching and thought part of the culture at Thapa, I would say is like to just always be giving back to the community to always be teaching what we've learned, like you'd be at stand up and someone would say, yesterday, I learned that something something about Postgres. And someone would immediately say you should blog that, or you should tweet about that, or you should or whatever, like you should give a talk about that. Like people are just like very much baked into the culture. And it was kind of thought bots answer to marketing, which was like how do you market developers well If you just don't even think about it as marketing, and think of it as teaching all the useful stuff, you know, it'll probably work out, okay. And indeed it did. So I came into this culture that was, like just primed. It was like, sort of good for me, because I was already primed to want to teach. And that was very much encouraged there. So I attended rails calm. So the speaking got started, at least when I attended rails calm for the first time, which is probably 2005, or not Seven, eight, who knows. And I thought it was so cool. I thought rails couples often was awesome. But I was like, I really want to be on stage. I want to teach people stuff. And so I applied to speak the next year and got accepted. And that began my like, conference speaking career. And it turns out, I loved it. I loved being on stage. I like helping people learn things. I think a talk is particularly fun, because it's teaching married with performance, which I really enjoy. So that has been kind of a huge thing for me, like I have, I have talks on YouTube from conferences that I gave in, like, you know, 2010 or so that people are still watching and still like commenting on and people still, like thanking me for talks I gave a long time ago. So it's been like this wonderful thing that has, it's like an asset that has paid back dividends to me for years and years.

Tim Bourguignon 26:09
I can confirm I wish to paraphrase this interview, I watched the song is Tokyo, how to talk to developers. This was energizing as hell, this was pressing off the standing on chairs, making people saying that was amazing. There was more performance and a talk I would say.

Ben Orenstein 26:31
Although, thank you. Yeah, that was that was my favorite talk of all time. That's that's the one that people mentioned to me more than anything else. If they if they say, Hey, I know that talk you gave it's basically always that one.

Tim Bourguignon 26:41
Yeah. And there was there was the the five minutes vim magic in the middle, just to legitimated as a technical talk, I'd say.

Ben Orenstein 26:51
That's right. Yeah.

Tim Bourguignon 26:52
It was really cool. It was really cool. Um, so you still you still doing this conference? road trip? I would say that another trip are still on the conference circuit?

Ben Orenstein 27:05
Not very well, I guess Actually, yes, a little bit. But in a new world. So I've stopped mostly stopped giving talks at developer conferences, although I'm going to probably pick that up again, in reasons for reasons I'll explain soon. But lately, I have been speaking at this conference called microcom, which is a bit of a new world for me, which is dedicated for people that are running small internet based businesses, which is what I'm doing now. So there's, I sort of found another community that I was interested in, which was okay, I'm kind of established in the Ruby world. But there's this whole world of people running businesses, and I want to be friends with them. And so I've kind of dedicated my conference attendance and speaking to that for a little while.

Tim Bourguignon 27:49
And you say, this is something you are going to do soon? Or is it?

Ben Orenstein 27:56
Well, so that this is what I have been doing. I haven't speaking at this sort of entrepreneur style conference, but I want to I think, possibly as a marketing effort for tuple, I will be starting to give technical talks, again, at developer conferences, to see if Hey, I can do this sort of the same thing I thought I did, which is if I give a great talk, and teach and show value and be useful when people say, Hey, I wonder what this tuple thing is, and maybe go sign up for it.

Tim Bourguignon 28:22
Yeah, very, very interesting. That's, that's a good way to go about it. I think. Um, would you be then talking?

Ben Orenstein 28:29
Yeah, well, we'll see. It might not work, but it's, it's something worth testing? Definitely. Would you get into it, talking about

Tim Bourguignon 28:36
pair programming and remoteness? Or would you pick a couple of different topic?

Ben Orenstein 28:42
Yep. Probably pair programming. Yeah, is sort of the most natural fit where it's going to be a useful topic for developers that's kind of naturally dovetails into, like, I can mention what what tuple is, without making it like a sound like an ad?

Tim Bourguignon 28:55
Have you had much experience working remotely?

Ben Orenstein 28:58
Um, no, I think it would be terrible at it.

Ben Orenstein 29:01
Why not? I

Ben Orenstein 29:04
I thrive on face to face interaction. So I didn't start a company until now because I didn't have co founders until now. And I knew that I would not want to do to try to start a company with someone remotely or by myself. I just I love being on a team. I thrive on a team. I thrive when I'm around people in person. And I just know that the constraints of remote work would be very bad for my mental health.

Tim Bourguignon 29:32
Do you have an idea how you figured that out about yourself?

Ben Orenstein 29:38
about myself? Um, well, I flirted with the idea once. So when I left football, there was actually a period of time where the time when I made the refactoring rails course, which was me trying to sum up my rails knowledge from the top out years. I was out of my own. I quit thought because I had been there a long time and loved it, but was ready for a new Challenge. And I didn't quite know what the next challenge was. So I just quit. And I made that course, as something to do to fill time and generate some income. But I was like working in a co working space and by myself, and it was just miserable. I just did not like it, like trying to do my own thing was was just not for me.

Tim Bourguignon 30:19
Okay, so you tried and figured out now? not my thing? That's, that's fair.

Ben Orenstein 30:24
Yeah. Yeah. And I'm much happier now like, so I have two co founders. We are not remote. We see each other all the time. And I love it. Like, I'm just, I'm just wired that way. I'm less extrovert than I used to be. But I'm still quite extroverted. And I just need that that time with people.

Tim Bourguignon 30:40
Hmm, that makes sense. Makes sense. Um, I would love to talk about podcasting a little bit. You said you were pretty early on the on the podcasting bandwagon and started the thought bot podcast. And how did that commas an idea? And how did you did you start with this?

Ben Orenstein 30:58
Huh? Well, like all the best ideas, someone else came up with it, and I have to take credit for it.

Tim Bourguignon 31:06
That's fine as well.

Ben Orenstein 31:08
Yeah, so so what happened was thought bought stop. I had an apprentice program, where we so much like that first job I had thought about wanted to hire experienced rails developers, but even thought couldn't find enough of them. So they started an apprenticeship program to train junior developers up to the level that they wanted. And one of the apprentices that we hired, was, had worked on. I think, Dan, Benjamin, this his name, had ever been a fairly well known podcast as a production person. And so when he got the thought out, he was like, Hey, you guys should have a podcast. And Chad, the CEO said, Yeah, you're right. That's, that's very much in line with our style. Like, we put out lots of free content to teach people things. And Chad came to me. And I'm guessing because of my, like, my public speaking, work, my conference talk stuff, and said, Hey, I think you would be a good host for this. Do you want to host the podcast? And I was like, and I don't know, like I'd be I'd be more interested to start like a SAS app or something, something that we can earn money, and I don't really want to edit it. I don't want to have to, like, worry about finding guests and all this stuff. He's like, No, no, no, you're just going to be the hosts, like, we're going to have someone else find the guests. Someone else is going to edit it. You have to show up and talk. And I was like, Okay, I'm interested. Let's do it.

Ben Orenstein 32:19
I can't do that.

Tim Bourguignon 32:22
So, so what was the what was the format? Like? Were you inviting people to talk about a technical product or technical feature or something? How do you prepare us?

Ben Orenstein 32:34
Well, it was a mix. So I hosted the podcast for five years. So there was a hole and the podcast, the topic of the podcast kind of followed my journey through Thapa. So in the beginning, I thought I was a developer, and I was most interested in like code. And so my earliest guests, were all prominent developers, experienced developers, and we would talk about really nerdy stuff, like the first episode of that podcast, I believe, was about the Law of Demeter. And so it started off very technical. And then, over time, I started actually ended up when I started up case thought, which you mentioned was a, like an online learning platform for rails developers. And so I was suddenly as opposed to writing code every day, I was trying to get a small business or a small business unit off the ground. And so my guess became entrepreneurs and people who were doing similar things. And yes, it was kind of like multiple phases to the podcast.

Tim Bourguignon 33:29
That's very interesting. So who is really? your podcast? in the in the company?

Ben Orenstein 33:36
Yeah, I was fortunate to be asked to do it. And then I got to, I got to shape it quite a bit.

Tim Bourguignon 33:40
That's really cool. That's really cool. And so let's jump to the other podcast that you are hosting. How did you come to how did you come to, to producing the art of the product podcast?

Ben Orenstein 33:51
Well, funny story. So after hosting, thought, bots, podcasts for five years, when I went to quit, they said, Great, Cool, thanks. We're gonna keep the podcast and you can go do something else. And so, which is fair, like they paid for it. That's it was there. I knew what I was getting into. That was that was the right call for them. But suddenly, it was like, well, I've gotten a lot of value. And I haven't mentioned this, but man, I didn't know how useful is going to be to host a podcast, because I got to make connections with so many interesting people in the industry. As I imagine you are aware, it's great. Most people will just say yes to podcast interviews, because it doesn't take a lot of time. And it's a good way to reach someone else's audience. And it's flattering. It's fun to talk about yourself. And so you can get lots of people to say yes to podcast interviews. And so we had tons of guests, and I got to become friends with a lot of influential people. So it worked out really fabulously for me. So I and, and also helped build that audience of people that, you know, knew about me and liked me and trusted me. So, when I left, I was like, well, I need a new podcast. And so I started another one. And thought it was kind enough to let me do an episode like a goodbye episode, where I said, Hey, I'm leaving. I'm not gonna be the host anymore. But if you want to follow on my journey, you can come listen to this other podcast. It's called The Art of Charm. And that was the initial audience that came with us, some of them. And it's grown from there.

Tim Bourguignon 35:06
Was that the continuation of your journey from developer to interviewing entrepreneurs? And then going on the other side?

Ben Orenstein 35:14
Yes. Yeah, I would say it is like, so now our product is me and my co host, Eric Rhymer, and both of us are working on startup companies right now. So we the podcast actually focuses on what we're doing. So I'm recording it in 14 minutes, actually. And we talk about like, what's what's what happened this week? Like, what are you working on? Like, how did this How did that email you sent worked out? work out? Like, what were the numbers, and we just tried to share the ups and downs of moving from like being a developer to starting a company yourself and, and figuring it out.

Tim Bourguignon 35:44
Very, very interesting. Very interesting. As you say, the time books is slowly slowly approaching the end of the time books. At the end of interview, always ask, same question, almost the same question. If you were to give yourself an advice, your former self and advice maybe when you were in high school, or maybe when you were in college, or after, after dropping out or being posed, unfortunately, forced and forcibly posed from college, would you give yourself as an advice?

Ben Orenstein 36:17
I guess, I mean, I, I don't know. Like it all worked out. Kind of okay. And so I might just say, like, yeah, heads up, like, don't worry about it too much. Like you're gonna figure it out. It'll be fine. Don't Don't sweat it too much.

Tim Bourguignon 36:29
That's a very good one. I love it. I love it. We always we always worry too much, I think.

Ben Orenstein 36:37
Oh, yeah. I spent lots of time worrying about things that never happened.

Tim Bourguignon 36:41
Yes, I do as well. And this today again, I'm guilty. astrology.

Ben Orenstein 36:48
Yeah, that's a fabulous waste of time.

Tim Bourguignon 36:50
Yes, it is. It is. Fantastic. Thank you very much. And if the listeners wanted to reach you, what would be the appropriate medium?

Ben Orenstein 37:01
Hmm. So I tweet a fair amount, maybe more than I should. On Twitter quite a bit. My Twitter handle is Rs 00. k, I was very into chess as like a 12 year old when I picked my internet handle and it is stuck around. So I tweet a lot. And I also podcast as we've discussed, and but my Twitter feed and my podcast are both very focused on the company and building now. tuple. So if you're interested in that sort of a company that sells to developers found by developers were figuring out how to actually make the company part not just the software part, you might find that interesting.

Tim Bourguignon 37:33
Absolutely. Anything else you want to plug anything coming up in the next month?

Ben Orenstein 37:39
A not quite my my tuple is going to be moving from private invite only to public launch, I think probably soon, we'll see I'm not gonna commit to a date yet. But if you're looking for a good remote pair programming tool that has very low latency, and is written by developers that hate bloated software, you might want to use that if you've been pairing, or doing a screen sharing with slack or zoom or something like that. And you want to try a nitpicky programmers tool instead, maybe check us out and see what you think. That's a tuple app to up Ellie

Tim Bourguignon 38:13
cressy, I will add the link to the show notes. So if you didn't catch that completely, just go in the shownotes and click on it. Fantastic. Thank you very much.

Ben Orenstein 38:24
My pleasure. It was fun.

Tim Bourguignon 38:25
It was indeed. And you have 10 more minutes to relax before jumping on your own podcast. Perfect. Thank you very much for your time and sharing your story. Thanks, Tim had a great time. And this has been another episode of developer's journey. And we'll see each other next week. Bye. Dear listener, if you haven't subscribed yet, you can find this podcast on iTunes, Google music, Stitcher, Spotify, and much more. Head over to www dot journey dot info. To read the show notes find all the links mentioned during the episode. And of course, links to the podcast on all these platforms. Don't miss the next developer's journey story by subscribing to the podcast with the app of your choice right now. And if you like what we do, please rate the podcast, write a comment on those platforms, and promote the podcast and social media. This really helps fellow developers discover the podcast and those fantastic journeys. Thank you