Creating Zeal Podcast

Ben Orenstein, Screensharing Startup Founder

August 16, 2018 Zeal Season 3 Episode 10
Creating Zeal Podcast
Ben Orenstein, Screensharing Startup Founder
Chapters
Creating Zeal Podcast
Ben Orenstein, Screensharing Startup Founder
Aug 16, 2018 Season 3 Episode 10
Zeal

Ben Orenstein, founder of Tuple, shares the journey from engineer to entrepreneurship and the origin story of Tuple. We get into why Tuple will be the best tool for remote pair programming and what Ben's personal goals for Tuple are.

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Show Notes Transcript

Ben Orenstein, founder of Tuple, shares the journey from engineer to entrepreneurship and the origin story of Tuple. We get into why Tuple will be the best tool for remote pair programming and what Ben's personal goals for Tuple are.

Additional Links

Chris White:

Welcome to the Zeal #interestings podcast. I'm your host, Chris White. Today I've got special guest, Ben Orenstein. He's the CEO of Tuple. Thank you so much for joining the podcast, Ben.

Ben Orenstein:

Yeah, my pleasure.

Chris White:

Super excited to have Ben on the podcast today. I think that there's an interesting story here of moving from a developer to an entrepreneur and I wanted to ask you all about that and ask you about Tuple and where that's going. Yeah, so, thank you so much. Can you give us kind of your personal background and kind of the story of how you kind of moved from being a developer to an entrepreneur?

Ben Orenstein:

Yeah, totally. So I think I've always had a little bit of a, of an entrepreneurial bent to me. So I've been a mostly Ruby developer for probably like 12 years now. Uh, my first professional Ruby job wasn't a proprietary or professional job for programming, wasn't a proprietary language that we shouldn't mention here, but eventually I made the transition into Ruby and I've been there for quite awhile, but while I was learning Ruby, I got really interested in Vim for awhile and after this was in the days of Peepcode, where Geoffrey Grosenbach was making like awesome screencasts for people and I decided that I would try to make my own Vim related screencast and so my first product ever was Vim for Ruby developers, or even for Rails developers, and it was just the Vim tips I had acquired while doing Rails stuff.

Chris White:

That's awesome. Does that still exist?

Ben Orenstein:

It exists in the sense that yes, like it's the bytes are together in a hard drive somewhere. It's not for sale anywhere right now, although honestly I think it probably could be like, it was fairly timeless. It looks dated now, but it's, there was, there was some good stuff there.

Chris White:

It sounds very timeless, I've been a Rails and Ruby developer for many years, but only in the last year have I started to really level up in Vim, become familiar, get kind of incorporate better techniques into that. So that sounds very personally interesting to me.

Ben Orenstein:

Interesting. Yeah. I think a version, I could be possibly convinced to do a version two someday.

Chris White:

Sweet!

Ben Orenstein:

But so I put that on on the Internet for $9 or, for sale, and sent an email out to like the Boston Ruby group and a couple friends and got the first sales notification of my life where someone that I didn't know purchased a thing from me on the Internet and, I feel like that really changed the course of my life in a way. It was just this amazing, like my heart started pounding. I was like, I was just, I felt like I was like walking somewhere and I feel like I just had to start running because I just had all this adrenaline in my system. All of a sudden it was like, wow, this is like the most incredible feeling ever.

Chris White:

You got an email notification and something changed in your brain.

Ben Orenstein:

Totally. Yeah. Yeah. And so I think, I think that was a bit of a turning point for me and it was a, it was a slow turning. It takes a while to turn the ship, but I think since that moment I've been like, this is really cool. I think my eventual destiny is to make this my full time thing and so there've been a number of moves throughout my career since then that have sort of sent me in that direction and I can talk about some of those if you want some more details.

Chris White:

Uh, yeah, definitely. I've listened to your podcast for a while, so I know some, some high level details. You worked for Thoughtbot for a long time.

Ben Orenstein:

Yeah, I did just about six years at Thoughtbot, which was a wonderful experience. And by the way, if you're looking for like a Rails/Ruby gig, or even sometimes not that, mobile development and other things now, they're doing the elixir and whatnot. That's a great company to work for, I was very happy there.

Chris White:

Very cool. So you've been a professional developer working for other people working for in consulting roles of various kinds. How does that wind up, did you gradually become more entrepreneurial in what you were doing or did you just kind of one day decided to leave, start doing your own things?

Ben Orenstein:

It was sort of a gradual process. So it started off? I think. So the, the, the screencast that I launched on the side was kind of the first clear thing. The next thing was probably I started doing these things with a friend of mine, Chris Hunt that we call code-cations, which is where we would go on kind of like a vacation together, but we would actually end up spending most of the time writing code.

Chris White:

That's awesome.

Ben Orenstein:

Yeah. This started on a whim based on just a random tweet and Chris and I discovered that we were good friends and we're compatible and so we ended up going to Costa Rica and renting a place like in the rainforest more or less and learning Clojurescript, uh, and--

Chris White:

Interesting!

Ben Orenstein:

--writing, interesting Clojure programs. And that went so well that we decided to make it a repetitive thing. And so a year later we kicked off another code-cation and while that was happening, there was this journaling service that I had been using called O-Life, that got shut down. And I was like, man, it sucks that O-Life got shut down. What if we just made a clone of that right now and charged for it. And he was like, yeah, sounds fun. And so code-cation number two turned into launch a, a tiny SaaS app really fast.

Chris White:

Really?

Ben Orenstein:

And Yeah. And it was, it ended up being really fun. And that to me is like when I really got like, got great was when I was like, okay, we're not just writing code, but like we're trying to solve a problem and try to get people to pay us for it. And that felt awesome. I really enjoyed that.

Chris White:

Yeah, that's really cool. So you spending a lot of time away from work with, with a close friend. Sounds awesome. But you are also engaging your brains, figuring out solutions to a problem and kind of getting that kind of classic entrepreneur's story were you kicked out something and so, what was that product? That was an O-Life replacement?

Ben Orenstein:

Yeah, so it was a little app and that this actually still is as a thing and people. We still have customers. It's called Trail Mix because we happen to be eating trail mix at the time.

Chris White:

Nice.

Ben Orenstein:

trailmix.life, If you want to go check it out. It's a very, very simple journaling service. So everyday you get an email from the app and it says how was your day? And you create your entry by just responding to the email and it builds that journal entry for you on the back end, but as sort of bait to get you to open each of the emails, we pick an old entry at random and send it to you.

Chris White:

Oh, interesting.

Ben Orenstein:

And so you have sort of this incentive to open the email and you get to read an old entry and it's crazy because you would think that you would even remember like an entry from three days ago wouldn't give you any surprises. But it totally does. Like it's, it's, it's crazy how your brain forgets things.

Chris White:

That's awesome. That's a really interesting hook because normally any kind of repetitive notification from, from a service is something that's super easy to ignore.

Ben Orenstein:

Right.

Chris White:

But if it has custom content from someone who you're a big fan of, which is yourself, that sounds like a pretty awesome way of keeping people on it.

Ben Orenstein:

Totally. Yeah. I, I, it's, it's worked for me. And that's why wanted to like, when O-Life shut down, this was, this was totally from their playbook, but when they shut down I was like, this is the only journal that I've, I've been able to keep consistently or semi consistently. And so I didn't want to lose that. And so we, that's why we replicated it.

Chris White:

That's awesome.

Ben Orenstein:

Because it worked for me.

Chris White:

Super Cool. So it's, the trail mix has been in existence for quite a while and other things have happened since then. Have you found that it's distracting to have something like trail mix in existence today or is it just kind of a nice thing to have around?

Ben Orenstein:

Trail mix is actually like a very simple APP and we've actively resisted adding things to it, like, a year went by and then we did another code-cation and we spent a few days adding like image support so you can attach an image to that email and, and have that image come back to you. Uh, and so we've expanded the feature set insanely slowly. We don't do anything to really market it and it, it, it chugs along making, you know, very small money but enough to support it and enough to keep it going. So it's not much of a distraction. It's very back burner for us. We basically have to upgrade the security or the upgrade that the dependencies when security vulnerabilities are found and very, very basic customer support stuff every once in awhile.

Chris White:

That's awesome. That's super awesome. I've heard about entrepreneurs that released very small apps and kind of keep iterating on them some are, you know, big explosions, some are, some are like very slow burning things and I think that there's a lifestyle out there where people release very small apps and continue to kind of iterate and keep doing it over and over again. But that doesn't sound like what you're doing today.

Ben Orenstein:

Yeah, that's true. Like with Trail Mix, or in my, my real thing.

Chris White:

Your today thing.

Ben Orenstein:

Yeah. My today thing. There's one more, one more detour worth mentioning I think, which is that during my time at Thoughtbot, so I started at Thoughtbot as a consultant and I was writing Ruby for other companies as you might expect. Because I had done a couple of screencasts on the side, I had some education experience and I was aware of that you can make money selling knowledge, uh, in particular to Ruby folks. And Thoughbot has a really solid brand, and a community.

Chris White:

Definitely.

Ben Orenstein:

And, we were starting to do some workshops and online workshops too. And so it was like, okay, now we have a couple of online workshops and Thoughtbot and I worked at like a revenue share agreement where they were selling my screencast and one day I went to a chat with the CEO, and I was like, you know, I think we should have, Thoughtbot should have an educational product and we should put all their courses under it and we'll charge a monthly subscription to it and I think we can grow a big community over time with our brand and all of the knowledge, like just taking the knowledge that's here and turn it into products. And he was like, yeah, I think you're right. Go do it.

Chris White:

That's awesome.

Ben Orenstein:

Yeah, it is awesome. And it's the, it's like a great, uh, that really typifies Chad's style I think, which is like, he likes ideas, he likes when people go for it. And he was just like totally in support, which was great. So that original idea became Upcase, which is Thoughtbot's education product, and I put that together, and other Thoughtbotters have come on and off the team. But I was kind of leading that team for the majority of the Upcase life, and that was my first really real go at it I guess, of, of, of creating a online subscription business that had real revenue and had a P and L and grew over years and that was like a really interesting phase of my life. That was great.

Chris White:

Yeah. Yeah. So if you don't want to say too much about how that went, that's okay. But how did your kind of personal relationship to that product go over its lifespan? Like it seems like there's kind of like the exciting launch process and then there's the continual maintenance and continual perhaps grind of, of continuing to add content and continuing to seek subscribe subscribers. Had your kind of relationship to that evolve?

Ben Orenstein:

It was tricky. I'm great at starting things like that's my favorite phase of any project is the early days.

Chris White:

Definitely.

Ben Orenstein:

That like sort of continual maintenance and keeping it going and sometimes finishing things off is trickier for me. That's not where I'm naturally strongest. And so I really enjoyed the early days of cases, particularly when we were growing a lot and there were like a good number of people on the team. But uh, there were times where it was either like me, the time that there was times when the team got small and there was less interaction, which is something that I need and also just got a bit repetitive so we signed up for like, Hey, we'll ship you weekly videos. And it was like wow, now we have like a serious content treadmill to maintain.

Chris White:

Gotcha.

Ben Orenstein:

And I just, after a few years of teaching people ruby and rails, like you get a little tired of ruby and rails. Like it's just, I think, I think that would be true for most people. And it definitely was true for me. So there was a point at which I said, all right, I gotta, I love running a product, running a product inside another company is an awesome way to learn how to do it. I thought that was like, that was like such a perfect middle ground for me. Like I was still making a good salary, I had a lot of safety and security. We had like the sort of the might of Thoughtbot behind everything we were doing, but I was getting to learn all these things and operating kind of as like an internal CEO of this product. But after a couple of years I decided I wanted to turn my attention somewhere else.

Chris White:

Uh, that's cool. That's cool. I think that that represents a ton of growth and I think, I think a lot of people will get into entrepreneurship and then find themselves very unhappy and not be sure why. It sounds like you kind of learned how to understand what your own personal motivation. Would you say, is that a good summary of that?

Ben Orenstein:

I would say that I am in the continual process of learning what works for me. So I'm, I'm always getting learning a little bit more about it and I'm also, I think it's worth pointing out, knowing what makes me happy and doing the things that make me happy are not the same thing.

Chris White:

I see.

Ben Orenstein:

So awareness is up, ability to act on that awareness is up as well, but not as much. It's sort of a lagging trend there.

Chris White:

So what things have you been doing lately to increase your happiness or act on things that make you happy?

Ben Orenstein:

That's interesting. So like one thing that I think helps is just by being aware of what's in your head a little bit more and so I've done various things to pay attention to what's happening in my brain because it's easy to walk around, lost in thought and not even and never step up one level and say, Hey, I'm lost in the thought. Like I'm spending a lot of time thinking about x and that x thing is stressing me out. And so I've done various mindfulness type exercises over the years. I've gotten pretty into meditation for a while. I liked the Headspace app. I also, right now I've been doing this thing called the five minute journal and where like, I spent a few minutes journaling in the morning and a few minutes in the evening just to kind of pay attention to the things that matter and asked myself questions like how could today have been better or what was great about today, like what, what would make today great and just pay a little bit more attention. That sort of thing helps a lot.

Chris White:

Yeah. One of the founders of Zeal actually gave everyone at the company a Five Minute journal last Christmas. It's actually been really, really helpful. Super helpful for me.

Ben Orenstein:

That's cool. Yeah, that's a nice gift.

Chris White:

Definitely. Definitely. Fast forwarding a bit, you left, did some other things for awhile. You launched another education product, if I remember correctly, right?

Ben Orenstein:

Yeah, so I, I left, so I was coming up with my six year anniversary with Thoughtbot and I was feeling like I needed to change. Thoughtbot was and is amazing, but it was just, I just couldn't think of a way to change what I was doing enough to make it interesting enough. Like I just wanted to just have something fresh happen and so I decided to leave not really knowing what to do and so the first thing that I decided to do was like, okay, I know how to make good educational Rails content and it was true, would be used to have nice to have a course that I've made to like bring in some revenue and that will hopefully fund me towards doing other things. And so I did. I made a course called Refactoring Rails, which I tried to distill down all my wisdom of like, okay, what do you do once you have a Rails app that's a little bit older, a little bit more mature, has a little bit more cruft to it, maybe. What are the refactorings and best practices and techniques that you can use to keep your shipping speed high. So it's still pleasant to work on in year two, three, four as opposed to like slowing down and being crappy.

Chris White:

Got It, got it.

Ben Orenstein:

So, so I shipped that course and that went well. Like had a good launch, continues to sell. I continued to get good feedback about it, which is awesome, but I was solo for all of that and I found a coworking space that had some and like made some friends and like joined some leagues and was trying to just recreate the experience of being in an office and having coworkers that I liked and it didn't really work. I'm like super, super extroverted. I do great on teams. I do terrible solo and I need face to face time. And so I was struggling and so I ended up taking a job briefly and calling like a temporary halt to my solo entrepreneur thing. Uh, and that only lasted a few months because I was like, the whole time I was like, okay, this is not what I want to do. I want, I want to do this thing, I just want to do it with people.

Chris White:

Got It.

Ben Orenstein:

I think my eventual destiny is to start and run software companies. And so like, that's, that's where I want to go. And so I was talking to this friend of mine, like every few days we would get together and we'll talk about various business ideas. And we were both, had an itch, we both wanted to leave our jobs. He had recently sold his startup to a larger company and was like stifled and not really enjoying the experience that much.

Chris White:

I see.

Ben Orenstein:

And so we finally hit on something and decided to pull the trigger.

Chris White:

Okay. Okay. And that thing is Tuple.

Ben Orenstein:

That thing is Tuple. Yeah. So basically what happened was, so Tuple is a Screenhero replacement or I should say it will be. That's our, that's our goal.

Chris White:

Got It.

Ben Orenstein:

Those are our marching orders. I was a huge fan of screen hero and I was kept talking to friends and saying, Hey, now that Screenhero is gone, what are you using? And there were never--I was never getting a great answer back.

Chris White:

Yeah.

Ben Orenstein:

It was always kinda like, well this is kind of as good or this is, this is okay. Or I've used a bunch of stuff and they both, they all kind of stunk. I actually listened to your recent episode. You did discussing this for like, a survey of the landscape.

Chris White:

What we found is that things were evolving, but there was never a very clear answer for if you're a pair of programmer working remotely, what do you use?

Ben Orenstein:

Exactly.

Chris White:

And the answer is you use a few things and it's mostly as good as Screenhero, maybe.

Ben Orenstein:

Yup. And that was, that was sort of my conclusion as well and other people had even like sort of harsher criticism of the market I would say where they're like, I've gone to like not even doing remote control stuff because it just, everything sucks.

Chris White:

That's true. That's true. I found that there are remote control options in the upstream, so we've used Slack solution. We've used Zoom, even try, we've trialed a few other things like Use Together, but what I've found is that the remote control aspect of those systems is not 100 percent as good as Screenhero and so instead of like observing that and taking action on that, what I found is that most of the pairing that occurs in our company is now just like no remote control. We're always just like, we're pairing, we're screen sharing. If I, if I want to interject, I just tell by my pair what I would like him to do.

Ben Orenstein:

Yeah. Do you miss the remote control?

Chris White:

That's a great question. I was at, I was thinking about that this morning and I think if, if remote control became like super good, super solid, again, I probably wouldn't use it with my current pair because my current pair has a very specific Vim configuration that I think would just not be very compatible with how I like to work. But I think that depending on the pair, I would probably enjoy having that remote control, especially if it was very seamless and very, very straightforward. Our company, there's just no standardization or, or any. There's very few similarities in how we have our environments configured. Some of us use Atom, some of this use Vim, I use Atom with Vim mode. Some of us use VS Code. I think that since Screenhero died, we've all kind of spread out in terms of how we'd like to do things. Uh, and I think that it's as a result of no longer doing any remote control.

Ben Orenstein:

Yeah. So I've, I've done pairing without remote control and I find that there's just a little too much dictating?

Chris White:

Right.

Ben Orenstein:

To get a point across.

Chris White:

The dictating part is pretty annoying.

Ben Orenstein:

Yeah. Like when I find myself like reading code, like dictating code to someone to type, it's like man this is not, this is not good. Like my, my ideal, like I like writing code, like with two keyboard's plugged into one machine. But that's where I felt like that's, that's like the ideal and I wish I could have exactly that remote. And so that's the, and that's kind of, that's basically where Screenhero got to and that's more or less that's where we hope to get to, too. Because I think when you're saying like, oh no like, curly brace, no no, the other one, not, not, no the one three lines down. And it's just, it's like that's, there's just a faster way of communicating. Like, let me just take control seamlessly for a second or two, show you what I want, and then move on. Or like I like being able to do things like ping pong pair programming where it's like, I write a test, you make a pass, you write the test, I make it pass. Like that's a really nice way to split up responsibilities and that's hard if like control is not really assessed, seamlessly switched.

Chris White:

Right, right. It would be difficult to ping pong pair where I write a test and push it, and you pull it, and you write the solution and we just switched. That would be pretty contrived.

Ben Orenstein:

Right. So I kept having this experience and everyone's like, no, there's no, there's no spiritual successor is basically what I discovered. And so I reached out to one of the cofounders of Screenhero and said, hey man, like I'm thinking about building something kinda like Screenhero could, could I talk to you for a little bit? And so he was very gracious and we did a call with him and we're like, do you think there's still a market here? And he was like, absolutely.

Chris White:

That's awesome.

Ben Orenstein:

And I was like, do you think Slack calls are gonna replace this? And he says nope. And so like we just got like all this like encouragement from him and also realism where he was like, it's, it's hard, but there's, I think there's definitely a market here and so we've got really, really energized by that call and that was, I think like the sort of the final thing we needed to be like, all right, let's, let's give our notices. Let's, let's take a crack at this.

Chris White:

That's awesome. That's awesome. So, so positioning wise, you're, you're positioning this as a tool for remote programming, like remote pair programming, at least initially perhaps? Or is that kind of like you're going to focus on that niche and stay in that niche?

Ben Orenstein:

Totally getting focused focus on stay there.

Chris White:

Gotcha.

Ben Orenstein:

I think like this is, this is the audience that we can reach well and can understand and we can evaluate it if we've, if we've hit our marks and I'm very happy to stay as a niche pair programming tool forever, I think.

Chris White:

That's awesome. That's awesome. So, so you want to be where, if people think I am doing remote pair programming. Oh you don't have Tuple, that would be a disappointing thing where it would be the clear solution that works better than everything else is Tuple.

Ben Orenstein:

Yes. That's where I want to get to. I want to be the most obsessed with the experience of using it and I think this is what made Screenhero so good with talking and talking to the Co founder. That's one of the things he confirmed as they spend a ton of time thinking about latency, latency in remote pair programming I think is kind of the number one thing to think about once, you've done that already really hard things have dual pointers and good keyboard control, which is also hard unfortunately, but latency, is like, when I'm typing on someone's machine and it's like if, if it takes too long to get that feedback when you're typing it becomes really painful and hard to do.

Chris White:

Gotcha.

Ben Orenstein:

So you have to really go nuts about that.

Chris White:

Yeah, I've noticed that it does not take much latency to turn it to take it from, I'm typing on your computer to I'm sending emails that show up on your computer screen.

Ben Orenstein:

Yes, exactly. Yeah. And so that, that to me is our, is our sort of our marching orders. It's like, okay, we have to care about latency more than anybody else and we have to do that because we care about pair programming because we want people to type on people's, other, like on remote machines all the time. And so the hope is, my hope is that if we are obsessed with this to a level that no one else is willing to go to, we can build a better solution to this than anyone else can. And then we will become the default answer and the spiritual successor.

Chris White:

Got It, got it. So pair programmers are your audience. Who are your customers?

Ben Orenstein:

It's a good question. So we actually do have customers already, which is awesome. So I've been,

Chris White:

That's awesome.

:

--recruiting people into, into our alpha, despite the fact that we don't have a working outlet to give them. Uh, but which is, that's extra awesome. Yeah, it's extra. It's very awesome. It's, it's really good validation. It's like, okay, yes, we are solving a problem. People want to have be solved to the point that they're willing to pay for it now to sort of help fund development and make sure it actually gets created. So that's, that's been really encouraging. But our customers right now are a mix. I would say some of them are people that are like freelancers that work remotely with lots of clients and want a good rock solid solution for this. But more and more we're setting up teams actually standing up teams of three, four, five, six people that pair internally amongst each other. I think our ideal customer is going to be something like that. A mid sized team that is remote and increasingly remote or going remote is going to be kind of our sweet spot I think.

Chris White:

Yeah. Zeal is having a huge transition week this week. Three years ago, our founders leased a very large office and Medford, Oregon. It was like 3000 square feet, had tons of room. They set up great desks where, very tall standing desks with room for, you know, two programmers to stand at. In the last six months, it was used daily by about three people, because we, we've, we've become more a remote team than not a remote team and so we, we just this week moved out of that office and the, the physical location of Zeal is now a smaller, more appropriate office to the amount of people to actually work in person and so we are an increasing, we are growing increasingly more remote as a team.

Ben Orenstein:

I think you're representative of a larger trend and that's one of the things that makes me excited about this particular niche is, I think programmers are going to go increasingly remote and we're going to seem like we're gonna see more programmers every month, which is good for us.

Chris White:

Definitely.

Ben Orenstein:

And we're going to see more programmers go remote every month and I think that is mostly a good thing for the world. It's nice to let people work from where they are. It has a lot of hiring advantages, but it does come with some disadvantages and so I think there's a nice opportunity for tools that help reduce those disadvantages and being able to remotely pair I think is totally one of them.

Chris White:

That's awesome. That sounds super awesome. Super good trends you. One thing that I wanted to ask you is what are your personal goals for, for this new company? You're interested in entrepreneurship, you're excited to start new things and work with your friends. Do you even have an idea of what you would like to be doing in like three years or five years, with Tuple?

Ben Orenstein:

We have a rough idea, so my co founders and I have. We had some heart, like plenty of heart to hearts before we get going to make sure that we wanted roughly the same thing.

Chris White:

That's awesome.

Ben Orenstein:

Yeah, and I think essential. Our plan as of right now is to not take funding. Like we're, we're bootstrapping this. We all have savings and so we're just trying to make it work with what we have.

Chris White:

Cool.

Ben Orenstein:

We want to grow at a reasonable pace and the three of us, I think basically aspire to a nice lifestyle, so we don't anticipate hiring a ton of people, trying to get really big. We want to make a really good thing that we're proud of. We want it to be the best when it comes to latency and usability and all that, but we don't want to, we're going to try to avoid creating a huge team to do it and we want to work reasonable schedules and stay sustainable and have... to me, if you build a successful that requires you to work a million hours a week, like why is that, like you've kind of. To me that would be a failure, right? Some people might be into that, but that, that, that to me would not be cool. What I want is a sustainable, profitable company that we can still be worked a little bit less on and that sort of that is, you know, maintains our lifestyle and is good, but it's not something that we're going crazy on all the time.

Chris White:

Right, right. So your goal is to make Tuple just large enough to accomplish your engineering goals and kind of support your customers well.

Ben Orenstein:

Totally.

Chris White:

But, but also enable you to have the freedom and lifestyle that you want.

Ben Orenstein:

Yeah, that's, that's about it.

Chris White:

That's awesome. That's awesome. So, so you could probably see yourself doing that for quite a while if that works out well.

Ben Orenstein:

If it works out. Yeah. Yeah. I mean, like I said, like they're, they're actually a lot of hard problems. This is by far the most technically challenging thing I will have built. I'm a web app developer, so like um, if this were like a, a CRUD app, we would be halfway done already.

Chris White:

Right, right. Sometimes you can ship a product in a, in a weekend.

Ben Orenstein:

Exactly. This is like real time screen sharing, so it's like it's sensitive to the Internet, it's sensitive to a lot of like, it's, we're talking milliseconds matter, and yet the operating system doesn't really want you to have multiple pointers and doesn't really like multiple keyboards controlling a thing. And so there's lots and lots of technical hurdles to jump and we're building it as a native app on Mac OS, which is not a, an environment that any of us have done anything on already. So there's a lot of hard things about this. So this is a longer shot, than other things I've done. Like Trail Mix we built in like two days and then it shipped and a lot of the other things I've done have felt very squarely in my wheelhouse and I was pretty sure I could do them and I just had to execute, you know, fairly well. This is, this is by far the hardest. And so hopefully, hopefully it works out like we're trying. We're, we're all all in. But I'm also realistic like this is this a challenging problem. And other people have tried to solve this and not succeeded. So it's, it might, it'll be hard and that's okay.

Chris White:

That's awesome. That's awesome. It's cool to,it's cool to understand like that you are going through a challenging thing and that you, you intend to succeed, but there's a chance that you might not. And I feel like having that understanding of that with your partners and understand long term visions and things like that, I feel like those conversations tend to happen too late, when I've talked to other entrepreneurs say had different intentions going into the product and they never talked to their partners about that.

Ben Orenstein:

Yeah.

Chris White:

And then that becomes a something ugly later on for sure.

Ben Orenstein:

Yeah. I could see that being pretty deadly.

Chris White:

Yeah. Yeah. So, uh, I want to respect your time a little bit and we're coming up on our listeners' time, but I did want to definitely ask you about one great pair programming, pair programming tip that you've learned over the years.

Ben Orenstein:

Hmm, sure, it's a little one, but I think is worth sharing.

Chris White:

Sure, small tweaks are the best.

Ben Orenstein:

So when you're navigating, meaning, when your, your hands are not on the keyboard, don't point out your driver's typos right away. I think a lot of people when they're navigating, they, they assume that their job is like high powered typo spotting. And so as soon as you make a typo they will point it out. But I think what you can usually do is just keep your mouth closed and what I've found is that like probably 50 percent of the time the person typing sees it on the line and then fix it, goes back and fixes it, and a bunch of like 40 percent of the time on top of that, another 40 percent they noticed that right away when they run test or you know, try to compile or whatever. And then only 10 percent of the time do you say, oh it's that semicolon on whatever or it's that curly brace over here.

Chris White:

Yep.

Ben Orenstein:

And I think it's just worth doing because it lets your drivers stay in the flow. If your mind is on what's coming next and you have the sequence of events and you make a typo at some point and someone forces you to jump back, I think you can kind of lose where you're at.

Chris White:

Got It, got it. I found that to definitely be true in my pairing practice, like every time, I feel like interruptions or something that I have to kind of hold back and kind of make sure I'm not doing too frequently because I feel like it pulls people out of flow a lot and sometimes it distracts them or sometimes see if someone's not used to pairing, you can even like embarrass them or like get their hackles up, which is not a good a good way to pull someone into the pairing environment. Yeah, that's an excellent tip.

Ben Orenstein:

Thank you.

Chris White:

I need to be more aware, self aware of that.

Ben Orenstein:

Cool. I think it makes, it's a small thing but I think makes a pretty decent difference.

Chris White:

That's awesome. That's awesome. Well thanks so much for sharing your story. Ben. Is there anything that you would like to bring to our listeners' attention?

Ben Orenstein:

Sure. I mean if you want to check out Tuple, you can get on our list. That's where we're recruiting people for like our upcoming Beta and whatnot. You can go to tuple.app to sign up there and you can also read about how we're thinking about the company and how we want to build it. One other thing that is possibly interesting to your audience is I run a thing called the Code Quality Challenge and this was something I created when I first left Thoughtbot.

Chris White:

Cool.

Ben Orenstein:

It's a group of people we get together and we do it as a cohort and we spend 30 days thinking about or doing an exercise to improve the code quality of our apps. Twenty minutes a day for 30 days and so every Monday through Friday I send out a challenge which is like, okay, day one, update the, read me, see what's out of date. You know, if you have no reason to create a basic one, here's a, a skeleton you might use. That's like a. that's like day zero and it's, it's a nice thing we, it's, it's free and like the last cohort had 850 people in it.

Chris White:

Wow.

Ben Orenstein:

Yeah. We had a nice forum where this some good interactions. People like creating their own meetups and talking to each other and sharing tips and I've gotten a lot of positive feedback for it and it doesn't cost anything, so maybe check that out. It's codequalitychallenge.com.

Chris White:

Cool. Well we'll definitely include links in the show notes. It sounds like an awesome learning tool and also community. Totally. How has the community kind of grown out of that or it kind of--?

Ben Orenstein:

That's one thing I'm struggling with is that, after the cohort ends, there's no like, people kind of fade away.

Chris White:

Gotcha.

Ben Orenstein:

And so I wouldn't say I've created a lasting community that is like, existing between the cohorts, but that's, that's a goal for that. That's a longterm goal. I think.

Chris White:

So it's more like a summer camp kind of a kind of experience.

Ben Orenstein:

Yeah, yeah, exactly. Yeah. You get that month together with some, some smart motivated people and it's an a. and one, one thing that I've gotten, I've heard from people is they liked doing with their coworkers, so if you can get some coworkers on board, it's a. it's a nice way to go about it. You have your own, your built in cohort.

Chris White:

That's super awesome. We'll check that out.

Ben Orenstein:

Cool.

Chris White:

Thanks Ben. Ben, I super appreciate it and thanks again for listening everybody. If you want even more interestings, sign up for our newsletter. It's at codingzeal.com/interestings, we find all sorts of interesting things on the Internet, summarize them, make it really easy to consume, or you can follow us on twitter at @codingzeal. Thank you so much.

Ben Orenstein:

Thank you.