Episode 354 | The Art of Product with Guests Derrick Reimer and Ben Orenstein

Show Notes

In this episode of Startups For The Rest Of Us, Rob talks with Derrick Reimer and Ben Orenstein about the art of product. They cover Ben’s transition from full time work to working solo. Derrick talks about the changes to his life after the Drip acquisition.

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Rob: In this episode of Startups For The Rest Of Us, I talk to Derrick Reimer and Ben Orenstein about the art of product. This is Startups For The Rest Of Us Episode 354.

Welcome to Startups For the Rest of Us, the podcast that helps developers, designers, and entrepreneurs be awesome at building, launching, and growing software products, whether you’ve built your first product or you’re just thinking about it. I’m Rob, and Mike is out this week so I’ll be talking with Derrick Reimer and Ben Orenstein. We’re all here to share our experiences to help you avoid the same mistakes we’ve made.

This week, I’m very excited to invite Derrick and Ben on the show. If you haven’t heard of them, they co-host a podcast called The Art of Product. You might recognize Derrick’s name because he is the co-founder of Drip and he has been on this show a couple of times in the past. Ben Orenstein spoke at MicroConf starter this year and he’s maybe best known for hosting the Giant Robot’s podcast as well as being a prolific Ruby On Rails developer. He recently left ThoughtBot to go out on his own.

Without further ado, let’s dive right into the interview. Derrick, Ben, thank you so much for taking the time to join me today.

Derrick: Thanks for having us.

Ben: Absolutely.

Rob: Ben, before I even intro you, I want to start with a story. I cut you off before the interview started and you said, “Hey, I went to the emergency room this weekend.” I said really, what happened? What was your next sentence?

Ben: Have you ever heard of Acroyoga?

Rob: That is the best lead-in to an emergency room trip I’ve ever heard. Walk us through that, Ben, what happened?

Ben: Acroyoga, I guess it’s short for acrobatic yoga. The basic gist is it’s a partner practice. You’re doing a lot of lifts and things of that nature. On Friday night, I was sitting, basically. My partner was laying on the ground with his legs at 90 degrees, an L, and I was sitting on his feet and leaning backwards in a back bend. It turns out that this guy was basically too small to base me, that’s what he was doing was called. He just wasn’t quite strong enough to support my weight. The first time we tried it, I fell off to the side harmlessly. “Aw, that didn’t quite work. Let’s try that again?” He was like okay, we can try it again.

We really should’ve stopped at that point realizing he just wasn’t quite strong enough to do it, but we went for it anyway. The second time, he collapsed and ended up dumping me more or less back onto my head, backwards.

Rob: Ouch. Concrete?

Ben: No, we trained in this Aikido studio. They’re used to throwing people. There are mats which is good. But I ended up basically doing a back somersault over my head with a degree of mobility requirement that I don’t have. I heard all of the vertebrae in my neck pop and felt this intense strain on all the muscles that run from my neck down my back.

I rolled out of it and then came up and was like okay, I can feel my fingers, I can feel my toes, okay that’s good. Nothing’s tingling, I don’t see any spots, I don’t think I have a broken neck. But all that tissue and muscular tear on the side of my neck was basically on fire. I couldn’t turn my head to the left, I couldn’t look up or down, I could only keep my head perfectly straight.

I tried to walk it off for a few minutes and then I was like no, I’m going to go to the hospital. I did. They put me in a cervical collar and were like we’re going to CT scan your neck and hopefully there’s no bone damage. Fortunately, it turns out there was none. Just soft tissue stuff, which is great, because it will heal fairly quickly. I was definitely worried there would be bone problems or worse, spinal problems of some kind. Got off pretty easy, it turns out.

Rob: Yeah, cause that stuff hangs around forever. Anybody I know who’s had even these minor back injuries, it’s just decades of dealing with it. Well, that’s good news, man. Glad you’re okay.

Ben: Thank you.

Derrick: Do you regularly do Acroyoga?

Ben: I regularly do it over the last two weeks. I have fallen in love with it over the last handful of days. It’s super fun, except for the crashing on my head, I feel way more mobile and strong in interesting ways. I’m totally digging it.

Derrick: That’s cool. Do you think you’ll go back once you’re healed?

Ben: For sure. I learned some lessons, I got off kind of easy and learned some lessons along the way. Should’ve absolutely had a [00:04:35], should not have had someone who I outweigh by 50 pounds trying to support me, should’ve realized when it failed the first time that we should’ve either stopped or gotten a [00:04:42]. There were a lot of warning signs that I just brushed by that now I think will set off much stronger warning bells in my head.

Rob: Indeed.

I want to take a step back and give a little introduction of both of you guys. Derrick, my co-founder of Drip and now VP of Engineering for Drip at LeadPages, lives here in Minneapolis. Derrick, you’ve been on the podcast twice before, is that right?

Derrick: Yeah, I think so.

Rob: Yeah, a couple times. You talked about the code tree sale and then I don’t remember what we talked about the other time. Folks should be relatively familiar with you.

And then Ben Orenstein, formerly of the Giant Robots podcast, and now you’re out on your own, independent, and you actually were a speaker at MicroConf Starter Edition this year. We’ve all known each other for a few years now.

The reason why I had to bring you guys on is a couple things. One, because you’ve launched a new podcast, it’s called The Art Of Product. I think that anyone listening to Startups For The Rest Of Us who is thinking about building software products and going the SaaS route should take a listen to The Art Of Product. You guys are what, maybe 8 or 10 episodes in?

Ben: Yeah, about 10.

Rob: You guys have a good vibe. It’s conversational, you’re both developers. I almost said Rails developers but I know you’re not dabbling in Elm and Elixir and other things. Maybe you’ve always dabbled in those. I just think that for folks who want to hear an even more technical look at starting software companies and a technical look at building software, because both of you have done it now for a decade or more. The Art Of Product is a podcast for them to check out.

Have you guys been enjoying the first 10 episodes, has it been fun?

Derrick: Yeah, I’ve been having fun with it. I’m still surprised sometimes that people actually enjoy listening to us just talk about what we’re working on. But I know that personally, that’s one of my favorite formats when I listen to a podcast, just hearing what people in the industry are up to and the day to day things that they’re struggling through or having triumph over. It’s been fun to just keep chronicling our story and hearing positive feedback from folks on Twitter and stuff, it’s a good shipping, I think.

Ben: I would second that. I think the radio has gotten a little more interesting lately since I quit my job and went independent. Now, Derrick is working on a large, successful SaaS company and I’m working on a small product business. We have two interesting angles on making money online.

Rob: That’s cool. How would you summarize the podcast in a couple sentences?

Ben: It’s two dudes talking. A brand new, groundbreaking format that no one has tried before.

Rob: Right. But it works because both of you have personality, and you’re both doing interesting things which really helps. Not just in work, it’s like Ben, you’re in a barbershop quartet and you’re doing Acroyoga and occasionally falling on your head. Derrick is traveling, he’s always working on side projects, he has his blog. There’s a lot of stuff going on and I think that’s always—interesting people make interesting radio, that’s how I think about it.

Ben: I think one strength that we bring to the table is that Derrick and I both do a pretty good job of not filtering too much. We’ve had episodes where one or both of us had been really struggling or feeling really down and we don’t sugarcoat that, we don’t shy away from it. I quit my job about two months ago, I think it’s episode two or something and you can tell I’m reeling, basically. I was expecting it to be hard but it ended up being much more shocking than I anticipated. I’m super, super down. I’m not talking about what’s freaking me out and why I’m scared and what’s harder than I thought it would be.

I think we both do a pretty decent job of putting that out there because I think it’s good to have that kind of stuff exposed. I think it’s useful for some people to hear that and to understand what it’s like to try scary things and to realize that hey, if I’m having these feelings, I’m not the only person doing it. I’m not the only person that experiences things like this.

Derrick: Yeah, we joke that sometimes it just turns into a therapy session. I think a big part of that is trying to debunk the imposter syndrome that a lot of people experience. Even people who are “successful” or have been doing what they do for a long time still kind of go through the same struggles that you’re going through if you’re even newer to the industry or something. We’re always trying to be authentic and genuine. To me, I start having a lot more fun once I started breaking down those walls and just trying to put it all out there every week.

Rob: I think that authenticity comes across too. Until you guys aren’t too… you may have outlines but I guess the pretty loose, you don’t edit much inside the episode, you just talk and what comes out goes to tape. Is that accurate? That’s just my guess.

Ben: Yep, that’s pretty much on.

Rob: That’s cool, awesome. For folks who are familiar with the Giant Robots Smashing Into Other Giant Robots, is that the correct title of the previous podcast?

Derrick: That is, yes.

Rob: Okay, it’s long, so I just forget if it’s smashing or banging or something. Ben, you were the host of that for what, hundreds of episodes, right?

Ben: Yeah, I used to work at a company called ThoughtBot and we had that podcast launched about four years ago, I think. I was the host through that whole run, something like 210 episodes, somewhere around there. Around maybe 20 or 30 episodes ago, I brought Derrick on as a co-host. Other people had been co-host or I had done interview formats in the past, but the most recent incarnation was Derrick and I doing what we do now on Art Of Product.

Rob: Alright, cool. That actually leads into talking about the transition. You mentioned that you worked for ThoughtBot for the last several years, I think it’s a bulk of your professional career. You’ve just recently transitioned away from that full time work to being independent. You’re working on a product right now and have ideas for other stuff. Talk a little bit about that transition, what inspired it, how it’s gone, some of the pitfalls but also the fun stuff that’s happened.

Ben: Yeah, I was at ThoughtBot for six years. I was working on ThoughtBot’s SaaS apps. I had started one of them, it was called UpCase and I had ended up managing another one of them called Farm Keep. That was really an awesome experience. I had started off just as a consultant there writing Ruby, and then eventually ended up more on the business side which is exactly where I wanted my career to go.

I’d fallen a little bit out of love with programming at that time. I wanted sort of a new field and a new challenge rather than trying to continue leveling up my programming skills. Getting to start those businesses and run those businesses was perfect for me.

After a handful of years at that, it started to get a little too same-y. I’ve always, my whole life, thrived when I am pushing myself into different situations, especially with this deep learning curve. That’s when I’m happiest, when my pace of improvement is noticeable and I’m getting better at something all the time. I felt like I had run a lot of the experience and knowledge out of what I could do at ThoughtBot. I felt like I need to make some sort of change.

Honestly, I didn’t know fully what I wanted to do when I left, but I knew it was about time to try it. I talked to a bunch of people first, you included, Rob, and just said, “Hey, here’s roughly what I’m thinking, here’s my financial situation, here’s my background, here’s what I might work on. Am I crazy?” Pretty much everyone said no, you’re not crazy, this seems pretty reasonable. I decided to go for it.

After spending some time thinking about what my first effort might be, I decided to build a course. I ended up after my time at ThoughtBot with a lot of Ruby On Rails knowledge in particular about how to write good Rails apps. The first thing I’m working on is a course called Refactoring Rails which is targeted at people that have been working on a Rails app for maybe a couple years and started to see the pace of development slow down. This pretty much always happens, it’s almost impossible to not slow down. But there are a number of specific, tactical things you can do, changes you can make to your app, and features you can use or not use that will help make that slow down minimal.

My days mostly right now are cranking out videos. I plan out a video, and then record it, and edit it, and send it out to my list, and repeat.

Rob: So you’ve gone from hosting a podcast and writing code and marketing SaaS apps to recording videos and pushing them out. Is the work as fulfilling, is it more fulfilling, what is that?

Ben: I would say it’s not quite as fulfilling. I do miss programming, and there is a little bit of programming. The videos I’m recording are actually me writing code live and showing how I would refactor things. There is a coding component to it. I’m finding myself more and more missing that deep work of focusing on a programming problem for a whole day and just having the time race by. I find it harder to get into flow when I’m doing tasks like editing video or planning out a video. I think the results of this course might be that I want to get back into some sort of programming things.

Rob: Yeah, I could see that. Derrick, you and I talk frequently enough about the importance of allowing our developers on the Drip team to get into that deep workflow state. That’s something that I know you talk about the dopamine rush for you has always been pushing features into production, but I also know that part of your job that you have loved the most is being able to put the headphones on, sip the latte, and get into the deep zone and get a lot of code cranked out.

Derrick: Yeah, I think that’s the creative muscle that you’re getting to exercise. When you’re a developer, that’s like your natural form of creative expression. It’s hard to not have that as a certain element of your day to day. I don’t think it has to be 100% of it, but I feel like for me, it would always have to be a percentage I feel like, for me to feel like I’m exercising that muscle.

Rob: That makes sense. Do you feel like—maybe not the last couple weeks, because I know that you’re out of town last week, I was out of town a week before. I’m sure there’s a lot of stuff going on. Over the past three to four months as our team has grown up to when we were acquired a year ago we were at 3 engineers and I think we’re at 10 at this point. You have a lot more managerial roles, technical lead roles. Your role has expanded, I’ll put it that way. Do you feel like over the past three or four months, you’ve still been able to have moments where you do get in flow?

Derrick: There’s been moments for sure. It’s been less than it used to be, definitely. I will also say that I get a lot of satisfaction off of working with one of the team members, pair programming, I’m talking about that a fair amount on Art Of Product. It’s like being one of the developer and we’re working through a hard problem, and even if I’m not writing a lot of code there, I’m just doing more of the thinking, the thought process of solving a problem. That also tends to give me the same rush.

Just watching some team members be successful at balancing between the designers and the JavaScript engineers and seeing that whole machine work and knowing that I can push things in the right direction at various points to keep people unblocked. That definitely gives me some of that satisfaction as well. It’s a different kind of satisfaction, I think, and it’s hard to compare it to that true flow state.

Rob: Yeah, I totally agree. I had to make that transition as well several years ago because I basically stopped writing production code the day you locked me out of the repo.

Derrick: Oh yeah.

Rob: Code chains that I tried to make that Derrick rejected. I still miss it. I don’t regret the decision that I made to transition away from coding full time, but I absolutely miss those so many days when you can just, as Ben said, the day goes so fast because you’ll look up and you haven’t eaten lunch and you’re four hours past the time.

Anyways, transitioning back, Ben, off on a tangent a little bit. You were talking about your transition and that the work itself is a little less fulfilling right now. How has it been, I know one of the concerns you have that you voiced on The Art Of Product was that you were concerned you’d be isolated or feel isolated because you are an extrovert and you get motivated by being around people and being on a team. Do you find that you did feel isolated, and then how have you combated that?

Ben: Yeah, I definitely felt it. That was one of the things that came up in those early days. I was expecting that part to be hard because I know I’m an extrovert, but it was even harder than I thought it would be. The good news is I found some coping strategies that worked pretty well for me.

I quickly got a coworking space. Going to a place where other people are working and I can just chat with people even while I’m filling up my water makes a pretty big difference. It’s little things, it’s small interactions. I wouldn’t say I have any deep, new friendships at the co-working space. It’s just those little things like someone to grab lunch with, someone to get coffee with, someone to say hi to that really just energizes me in a deep way.

That helped. I wouldn’t say I’ve solved it by any means. When I’m recording video and editing it, I need to do that in a quiet space that has to be away from everybody else. Even when I’m planning out an episode, it’s a lot of deep work of writing and focus.

The co-working space has kind of worked as a hack. At the end of the day, no one’s on my team, it’s just me doing this effort and I’m the only one paying attention to it in a certain way. I wouldn’t say I’ve solved it, I think I’m still very much a team person. I like working on stuff with people. I’ve gotten some of that social interaction squared away and that’s helping, but I still feel at times a bit of a yearning for other people to care about what I’m doing and to be doing things with a group.

Rob: I think that’s a good point.

Derrick, you and I have talked. In the past, I know at one point you were a single founder and wanted to be the solo-preneur and run a small lifestyle business. After we started working together, we found the partnership to work so well. Then, we grew a team and we enjoyed working with our original team and now obviously the folks we’ve hired. How has your thinking changed, or has it changed on that whole running a company on your own versus more of what Ben’s talking about which is getting energy from the team? In future efforts, assuming you move on at some point to do another project, do you think that you’ll want to be solo or do you think you’ll want to have a team around you?

Derrick: That’s really interesting. I think it definitely has morphed my thinking about it. I feel like four or five years ago, I was all about how much can I do as one solo person, how many hats can I wear in the most strategic way so that I’m just captain of my own destiny, one person going solo. My feelings about that are definitely changed. Our collaboration with Drip, with working with the core team. It’s fun to grow the team and see the full actualization of Drip at a larger scale, but I still look fondly back at the days where it was a core team of five or six of us sitting in an office together.

That was really, I feel like, the sweet spot of working with a small enough team where you can all be in a room together, you can all bat around ideas. You have a lot of people on the team who are cross functional. Anna in customer success is doing a call, and then throws an idea across the room, and the developers are both sitting there and we kind of hash stuff out and get on a white board. Those kind of interactions are gold. It’s hard to imagine not at least having a small team like that with a future endeavor at some point. It may start out solo but yeah, I couldn’t imagine trying to wear all the hats and do everything on my own.

Rob: I think back to when I was working full time for the people. It’s funny because Ben’s insight into himself of needing other people around him obviously shows that, Ben, you know yourself pretty well. When I was leaving full time work, I was the exact opposite in the sense that I knew I didn’t want to be around people. The thing that I looked forward to most was going and working in my bedroom and never talking to anyone. I’m an introvert, it shows difference of personalities that even two software developers can have.

I think you don’t necessary fit the mold of the software developer who wants to go to their basement and code, you seem to really straddle multiple worlds, I think, with the extrovert and the personality and the ability to speak very well from stage as well as also having mad code shops.

Ben: I appreciate that. I’m not sure why that is, I guess I’ve just always enjoyed [00:21:21] skills. Since I enjoyed this deep part of the learning curve, I want to not just get really good at code and then keep getting better at programming, I want to be good at programming and then I want to learn how to speak in front of people and I want to learn how to run a business, and I want to learn how to market.

I think over a long time of doing all this, I’ve put together a handful of skills that you maybe don’t see in one person. I think maybe that’s the exception, people tend to focus on a thing and be like hey, I’m really good at this, I’m going to double down on this. Whereas I’m like hey I’m okay at this, I’d like to pick up a couple more skills that I’m okay at.

Rob: That makes sense. We’re going to do over, under here. I’m going to say ten years and both of you are going to say answer this.

Ten years, will you still be committing code to a production repo that people are using? Or, you can still work on a software company or be running a software company or whatever but ten years over, or under?

Ben: That’s a fascinating question.

Rob: I hate to put you on the spot. I was just thinking out loud. I just think it’s a fascinating thing to think about.

Ben: My guess is I still will be. There’s only been a handful of things that I have found so fascinating that they’ve retained my interest over a super long time. Programming has been one of them. I’d be kind of surprised to see that change. I think we’re at a renaissance of writing code for money and to provide value to businesses and things like that. I feel like this industry is only going to get more interesting. I think if I had to guess, it’s going to hold my interest and I’m going to want to still be making stuff directly.

Rob: So we get an over from Ben. How about you, Derrick?

Derrick: It’s an over for me as well. I feel pretty strongly, and I feel like this is not a hypothesis that I’ve totally tested. I feel like it is possible to still be the captain of a company, CEO as you may call them, and still be a person who contributes code. A traditional trend that you see is people starting out as a developer, writing the code, and then walking away from the code so that they can focus on the rest of the business aspect.

I think that is certainly one path you can take, but I feel like there is a secondary path where it’s like instead of totally giving up the code and focusing on marketing or what that other side of the business, I feel like you can still be a technical CEO founder and ultimately hire or get this through a co-founder, the marketing side of the business. I feel like you can flip that on its head so you don’t have to totally walk away from the code. I’m at least hoping that that’s a model that works because it’s hard to picture myself not actually being involved in code at all, I still can’t picture that that would look like.

Ben: Yeah, I have a quick anecdote that supports that. Six years ago, I went to interview at ThoughtBot and I was supposed to talk to the CEO. He’s like, “I’ll be with you in one second, I just want to get this test passing.” That had such an impact on me. I was like oh, I’m definitely going to work here. That is such a good sign. When the CEO is still doing technical work, he’s still technical but even more importantly, it means he understands what the life of being a developer is still. There’s no disconnect there, and that was awesome.

Also recently, Alex MacCaw who’s the CEO of Clearbit which is a company that I respect like crazy. I reached out to him on Twitter and said, “Hey, are you still writing any code for Clearbit?” He said, “Yeah, I wrote the feature that we’re shipping tomorrow.” It’s totally possible and I think it’s a workable model.

Rob: Mad props. Peter from Teamwork, he’s the co-founder. He still commits code to the repo and they’re over 100 employees now. They do about $15 million ARR or something like that, their SaaS app. I know there are folks out there that are doing that.

Ben: Yeah, so we’re both overs. Does that mean we shouldn’t start a company together, Derrick?

Rob: I think your skill sets may not be complementary, there’s a lot of overlap.

Ben: Rob, what do you think about that? Do you think, if I was like hey, I wanna get really serious about growing a SaaS company, is giving up the code something that I should consider?

Rob: It depends on what you mean by really serious. If you want to build a deck of million ARR SaaS company, I do think it would be something that I would consider. I think it would be the most efficient way to get there, just because coding at a certain point would become a distraction. It’s so hard.

If you’re going to head up a company, you become interrupt driven because you have to drop everything when people Slack you. I just can’t imagine enjoying coding. You can probably still get some code written, I just can’t imagine enjoying that when people are pinging me on Slack because they need an answer or stuff’s going to fall over in the next hour.

Ben: If I wanted to pair up with somebody, I would either be looking for someone technical to head up the technical stuff or the other stuff to head up that side. In your mind, is finding the technical co-founder an easier thing to do than the opposite?

Rob: Boy. I think for you, since you could do either but you enjoy the code more, my opinion would be that you should be able to find someone to do operational stuff. Since you would be so opinionated about the code in a good way if you’re running it, but in a bad way if your co-founder is running that. You could imagine the arguments or the disagreements that emerge from that.

Personally, I think if you do still want to stay in the code, I don’t think that’s a terrible choice if you can find somebody who can be the operations person. Hopefully, I think as Derrick and I found, hopefully someone who may be used to be a developer and doesn’t want to write code anymore and does want to walk away.

I feel like part of the power of Derrick and I’s partnership is that I am technical enough. I wrote production code four or five years ago. We still can have really in depth conversations, especially in the early days when it was just the two of us and he could talk to me about detailed stuff you can’t talk to a non-technical person about. I feel like that might be, just seeing Derrick and I’s model work, that might be the perfect fit for you.

Derrick: Yeah, I think you and I overlap in all the right ways. I care about the business side and I actually want to be involved in the business strategy conversations, but my main focus is the code. LIkewise, you’re predominantly thinking about product and operational type of stuff for the team but we can sit down and hash out like alright, here’s what I’m thinking for this architectural piece. We talk stuff through, and those are usually productive conversations as well. I feel like we both step into each other’s territory but not in a harmful way or clashing way, but just in a very complementary way.

Rob: Yeah, I think we’ve had conversations where if we do wind up, we both have opinions on all the areas of a company or the product. If we wind up disagreeing about something, I will absolutely be like this is a technical decision and it’s yours. I step away and I don’t feel like I have any more insight into it. I feel like I have a lot less insight into it and that Derrick has the ownership and the responsibility of it.

Derrick, we’ve covered Ben’s transition away from full time work to independence. Just about a year ago, I guess it was about 13 months ago, you and I sold Drip to LeadPages. Month or two later, we moved to Minneapolis. What’s new in your life?

Derrick: Obviously, moving is a big step for me. I never lived outside of the town that I was born and raised in. I’ve been taking this as an opportunity to experience something new. I definitely don’t regret the decision. Minneapolis is an awesome city, we’ve been getting to enjoy everything that comes with living in a really world class city, that’s been a great experience. Also, just joining a company of 180 people has been great learning experience too.

Most of my work experience prior to that has been at small companies, so I was at a small family business in college that I worked at part time where it’s just a few of us in an office, and then obviously Drip grew to 10 people. To be part of a large organization is a fascinating experience to observe and see how things operate and see how many of the things that we figured out along the way actually translate well into a large organization. Yeah, it’s been a fun ride.

Rob: What do you think has been the hardest thing about the transition for you personally or professionally?

Derrick: I think the biggest struggle is probably all aspects of scaling the company. The technical side, we’ve been dealing with quite a bit of database issues and queue issues. These are all things that come with the territory of growing the business like this. When you’re acquired and now you suddenly have thousands more trials than you had before, these are all things that are naturally going to happen.

It’s been, I would say, a period of very aggressive learning where you have to be on the ball all the time of looking around the corner for the next scaling challenge. It’s been pretty exhausting, I’ll say. I think I felt that recently, and the vacation I took this last week has helped me. I think I need to do a little more of that because it’s been a pretty intense year of just learning and working through scaling challenges.

Also, growing a team. We now have a development team of ten folks. We’re very picky in our hiring. The hiring process was pretty long to get the team out to where it is today. Just figuring out how to scale myself and de-couple myself from processes where I normally had been previously deeply involved in has been a challenge, but a good challenge. It’s good to see the team start to take responsibility for things that I normally would’ve been squarely on my shoulders.

Rob: Yeah, I would agree. I think that’s been the hardest part. Moving to a 180 person company when we first moved here, coming back to the conversation earlier about introvert versus extrovert, it is interesting that although I am introverted, when I wanted to go solo or go out on my own I didn’t want to work with a bunch of other people. But by that time that we had grown Drip, I really enjoyed working with you guys. I moved here and I was the only one from the Drip team just sitting in the corner on my own and that felt super lonely and isolating. As you one by one started showing up, it was like oh, this feels so much better. It’s good to have the team around.

Mixing things up a little bit. Ben, I wanted to come back to the course you’re working on. You mentioned your video course, is it Refactoring Rails?

Ben: Yes, that’s right.

Rob: I’m sure there’s some folks listening to this episode that want to learn more about it, potentially check out, maybe you could give away a couple of the videos so people could hear about it. Where is that, what URL?

Ben: refactoringrails.io.

Rob: Cool. You’ve been working on that for a couple months? Are you releasing that as you go, or is that a launch day coming up?

Ben: I’ve been releasing samples. I have 4 videos done out of what I expect to be about 10. Making progress, chipping away. Every time I finish one, I send out either the whole thing or part of it to the people that are on the launch list. It’s been dripping out steadily.

Rob: Very cool. refactoringrails.io. You’re using Drip for that launch list, am I right?

Ben: 100%.

Rob: Alright.

Ben: After most of Art Of Product episodes, I get free tech support from Derrick.

Rob: Totally.

Derrick: If you want a main line to the co-founder of Drip, you just got to start with our podcast.

Ben: I have a quick question for you, Rob. Actually, speaking of free tech support, this is actually free marketing support. I believe, by default, when I make a campaign in Drip, it has this option checked so it will only send emails to people in their local timezone at 11:00AM or something like that. I’m not sure if that’s a default but I have it checked on one of my campaigns. Would you call that the best practice? Is that typically going to give good results, or do I need to not worry about that?

Rob: I would say yes, it is the best practice in terms of all the split tests and experiments I’ve done over the years. That’s kind of a default. It depends on what time is on your end. If you’re on the East Coast, you don’t want it to be too early for people on Pacific, so I would tend to go a little later, maybe around 11:00AM, between 10:00AM and noon, probably. Whereas if I’m on Pacific, I might go a little earlier.

But to be honest, if you’re one or two hours or three hours off, you’re going to see very small difference. At our scale, meaning thousands or tens of thousands of people on the list, it kind of doesn’t matter. I wouldn’t be super worried about it. You can, of course, run the split testing in Drip and you can test that out on your audience but I bet you probably either wouldn’t have enough clicks to actually get a statistically significant answer or it would just be so similar if you tried 11:00AM versus 1:00PM or something.

Ben: That’s kind of what I figured. It kind of comes down to almost just my impatience. I’ll finish a thing on Friday at 3:00PM, and I’m like ah, no one’s going to get this until Monday at 11:00AM, I want the feedback faster.

Rob: You can try sending a broadcast right when you get it done Friday at 3:00PM and just do a poor man’s split test. You know your historical, you can look at all your opens and all your click rates, just try it once and see if it tanks.

I know that accidentally one time, this is pre-Drip, I was in Mail Chimp and I scheduled something. Instead of 10:00AM, I scheduled 10:00PM. It was not good. It was buried in people’s inboxes. When they went to delete, it wasn’t near the top as they were working. I remember the open rate being substantially less. I ran a couple other experiments where I sent at an odd time and sometimes it hurts and sometimes it doesn’t matter. I think generally, during the day for a work audience is pretty good.

I ran a job website at one point. It was Sunday. Everyone thinks about applying for jobs on Sundays because they hate their jobs. There would be this big spike in traffic and that’s where these emails would get the most traction.

Ben: Makes sense.

Rob: That’s it, cool. refactoringrails.io. Derrick, you have a blog at scalingsaas.net that you don’t update very often, is that right?

Derrick: I’m going to correct you, scalingsaas.com.

Rob: Oh that’s right, you got the .com.

Derrick: Yes, I wanted to blog more than I actually have which is why podcasting has been a good medium for me. But I do occasionally crank out a post here or there. scalingsaas.com, you can follow me in text there.

Rob: Sounds good. Gentlemen, thanks again for coming on the show. If folks want to hear more from you, they can head over to The Art Of Product podcast.

Ben: Thanks for having us.

Rob: Absolutely, my pleasure. That wraps us up for today.

Our theme music is an excerpt from We’re Outta Control by MoOt. It’s used under Creative Commons. You can subscribe to us in iTunes by searching for Startups and visit startupsfortherestofus.com for a full transcript. Thanks for listening, we’ll see you next time.

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