How Three Founders Created a Profitable Business That They Haven't Even Launched Yet with Ben Orenstein of Tuple

Ben Orenstein 58s

Thanks, man. I'm super excited, too. I've been listening to the podcast for a long time so I'm super psyched to be a guest on it.

Courtland Allen 1m 4s

Well, I like having founders like you on the podcast, Ben, because you are actually in the thick of things. You're not remembering what happened five or six years ago. You are working on it right now. A year from now, Tuple could be a wild success. A year from now, Tuple could be dead, and you've moved on to something else. We don't know. You're in the middle of it.

Ben Orenstein 1m 21s

Yeah, it's real life drama. It is reality television happening now.

Courtland Allen 1m 25s

That's exactly it. And I can tell you I've been surveying different segments of the Indie Hackers audience a lot recently and the vast majority of people listening to this right now are way earlier than you. They have not started their businesses yet. They are perhaps tinkering on side projects. They haven't launched yet. They aren't charging anyone. So, I'm excited to dive into your recent experiences, Ben, because the things you've been grappling with for the last year are the things that everybody else is going to be dealing with very soon. So, perhaps the best place to start here is to point out the fact that you were a software engineer at Thoughtbot. You got to do a lot of public speaking, a lot of coding. It was a very cushy job with a lot of autonomy and I'm sure a great salary. Why would you ever give that up to start a business?

Ben Orenstein 2m 5s

I guess because it sounded fun. I am very much addicted to trying new things that I'm not good at yet. I like to say that my favorite thing is the steep part of the learning curve. I tend to stay involved in a hobby or something as long as I'm making rapid progress and getting better quickly. And then once I have gotten my feet underneath me and I can see, now it's just a bit of a slog to get to actually great at this, I usually lose interest. Hopefully that won't happen here. I'm hoping that starting a company is dynamic enough that there's enough new things I can jump into that it doesn't become boring. My hunch is that that's the case.

Courtland Allen 2m 40s

Yeah. I was actually planning to ask you what would have to happen for you to regret this decision of becoming a founder. I think your intuition, your hunch, is spot on. It's probably not going to get boring. It's never going to be easy, that's for sure.

Ben Orenstein 2m 52s

I don't think I could regret this. So, I'm a year into it now and honestly this last year has been more interesting than several of the previous years combined, I would say. And I'm very lucky. I had a great job and it was an interesting job. My happiness level and baseline back then was very high. It was great, but this is even more fun and even more interesting. So, if all the numbers turned south tomorrow and we just went down to zero, I wouldn't look back on this and be like, “Oh, I shouldn't have given that a shot.” It'd be okay.

Courtland Allen 3m 21s

That's cool. You were already happy before. Now you've broken through and reached an even higher high, and you're not even that worried about failing. And I think if you could take that zoomed-out perspective and say, "You know what, no matter what happens, it's all gonna be fine," then it really makes it easy to just appreciate running your startup in the moment.

Ben Orenstein 3m 37s

Yeah. And it was interesting, when I first started doing this, I would tell people what I was doing and they would say, “Wow, that's really brave of you to take a big risk.” And honestly, I didn't feel that way at the time. I didn't feel like I was taking a big risk. It's like I have development skills and so I have a pretty reliable thing to fall back on. It was a risk in the sense that I was eating up my savings and I couldn't deploy that for something else, but it didn't feel like the end result of this would be, “Oh, maybe I can't pay rent,” or some horrible thing is going to happen to me. I won't be able to go to the doctor or something. It was more like, to me, the bigger risk was regretting not doing it.

Courtland Allen 4m 14s

So what was it like making that decision to quit your job? Was it a spur of the moment thing or was it something you had been turning over in the back of your mind for years? How did that go?

Ben Orenstein 4m 24s

It was a little bit of both, in a way. So, it had been on my mind for a long time. I had been feeling for a while, maybe like five or six years, like my eventual destiny was to start my own company. It just seemed like the ultimate expression of challenge and interest and applying my skills to a thing that I was fascinated by. It seemed like I was going to do this eventually. In some sense, it did not sneak up on me. When I did eventually leave my last job, that did happen kind of quickly, in that, over a couple of months, I just got the itch. I just got dissatisfied and I was like, "You know what? I think now is the time." I’ve been saving money for a long time and I don't actually know what I'm going to go do. I didn't have the idea, but I just knew that I didn't want to spend any more time not trying something. It was really over just a handful of weeks where I decided to pull the trigger.

Courtland Allen 5m 14s

The saving money part of it is so important because it just takes a lot of the stress off. It gives you peace of mind. I did the exact same thing. I had been contracting for a couple of years. I had a year, year and a half of runway saved up and this made it a lot easier to quit. Like you said, having development skills to fall back on is a pretty good form of insurance as well.

Ben Orenstein 5m 31s

A hundred percent. I think if your audience – so your audience is possibly aspiring to do this someday. One of the key things I would encourage them to be doing now is actually just saving money. Just get your expenses as low as you can and start putting away some cash. I have two co-founders and the three of us, all at the beginning of this said, "We can go at least a year with the savings we have." That was so useful for us. And now, because we're basically at ramen profitability now.

Courtland Allen 5m 59s

Oh, congrats. You're already there.

Ben Orenstein 6m 1s

Thank you. Yeah, I think basically this month it's going to be – that's true if the numbers keep going where I think they will. And we have all of our equity, so we split the company evenly and we didn't have to give any of it away. And it's just like, wow, if we hadn't had that savings, we could be in a very different position right now.

Courtland Allen 6m 17s

That's one of the best parts about bootstrapping and being an Indie Hacker, is you have 100% control of your business. You can do whatever you want. You don't report to anybody and you don't have to beg any gatekeeper, investors for permission to follow your dream. And I think having savings is really what makes that possible for a lot of people.

Ben Orenstein 6m 32s

Totally. And there was sort of an interesting – there was a point that made this very clear to me. Originally, I was going to have one co-founder and the third co-founder sort of appeared, last minute, right before we were getting started. One of the key questions that we had for him was, "What's your savings situation? Can you go a while without getting paid and without raising funding?" And because he said yes, it was easy to add him to the team. And if he had said no, I don't know if he would be with us on this journey, honestly.

Courtland Allen 6m 59s

Let's talk about this process of vetting a co-founder because this comes in the Indie Hackers community all the time. "Hey, I found somebody that I might want to work with, but how can I be sure that they're the right person? How do I vet them? What kind of questions should I even be asking?" And it's kind of a crap shoot because people are complex. You're not sure how they're going to change over time. It's hard to know what to ask. How did you decide to pick your particular co-founders, Ben, and how certain were you that they would work out?

Ben Orenstein 7m 22s

Well, so one I did the right way and then one I took a bit of a leap on. So, I have two co-founders, Joel and Spencer. Joel and I have known each other for years now, probably six years. We actually met through singing. We both sang in a barbershop chorus, which is like an acapella men's singing organization. We were friends for a long time. He previously started a start-up and then sold it to another company and was getting bored himself. Originally, he and I – I would go to his house and pitch him on various business ideas. One day I pitched him on the thing that became Tuple, and he said yes. So, that was the traditional or I guess the recommended approach, which is start a company with somebody you know really well.

Courtland Allen 8m 1s

Yeah.

Ben Orenstein 8m 1s

So I had no stress around that. I knew Joel and I liked each other, and I was confident we could work through any problems we had. Spencer joined the company – he joined before we were a company. But basically, as Joel and I are ready to quit our jobs, Spencer quits his job and reaches out to Joel and said, "Hey, I just quit my job. I'm trying to figure out what to do with my life. What are you up to right now?" Now Spencer had worked for Joel at Joel's previous startup. So, Joel had a relationship with Spencer already and so Joel comes to me and says, "Hey look, Spencer's free. He was great. I think we should seriously consider adding him to the team." We met with Spencer and we talked about our philosophy, I guess. What kind of company do you want to build? Do you want to raise money and try to make this thing huge? Do you want to build something smaller and at a little more sane pace? And just made sure that we agreed at a lifestyle level of what we were looking for. But at the end of the day, I was more or less just trusting Joel's judgment and hoping it all worked out. And got lucky. Because, shockingly, in a year of working together I feel like we've had almost no conflict. It's been ridiculously idyllic in a way.

Courtland Allen 9m 6s

The role that luck plays, is so fascinating to think about. This could have easily gone the other way. If you guys were at each other's throats, fighting every day, disagreeing about the direction of the company, and you guys split up months ago, it wouldn't be that surprising of a story. To my mind, luck is really just anything that's out of your control. Anything that you placed in somebody else's hands, anything that you didn't really think about, just sort of happened. Anything you can't control. How much can you really control another person? Even if you vet them, how much control do you really have?

Ben Orenstein 9m 32s

Talking to my mom about this, she's a therapist, and she says there's a degree to which successful marriages are their result of luck. Because if you get married at 25, you basically can't tell what that person's going to be like over the long term. If you're lucky, you pick someone who grows in a way that's compatible with the way that you grow, but you can just as easily not.

Courtland Allen They don't even know how they're going to turn out another 10 or 20 years.

Ben Orenstein 9m 57s

Yeah, exactly. Absolutely. You can't promise that you're not going to do that.

Courtland Allen 10m 1s

No, you can’t. So, let's go on to these early stages of you starting Tuple. You said that you would go over to Joel's house and you would pitch him on this list of startup ideas you had.

Courtland Allen 10m 10s

What were some of the ideas that you have on this list and how did those conversations go?

Ben Orenstein 10m 14s

I actually have my list of business ideas, which I just have as a note on my phone. Do you want me to just read you some of these?

Courtland Allen 10m 21s

Yeah. Let's hear them.

Ben Orenstein 10m 22s

All right. Quality analysis for Rails apps, which is like Code Climate.

Courtland Allen 10m 25s

Okay.

Ben Orenstein 10m 26s

SaaS in a box Rails kit. So, a tool for spinning up a SaaS really quickly. A Rails app that's preconfigured. Some of these are very generic. Paid Ruby gem for something.

Courtland Allen 10m 37s

For something?

Ben Orenstein 10m 38s

For something. Just charge for code for something. (Laughs.) So, it's a mix. And then some of these are more like consulting-y, like webinars as a productized consulting service. The short answer to this is, none of these really caught us, honestly. Some of these are okay. I sort of like thinking of business ideas just as a little hobby. But that doesn't mean that any of them are any good.

Courtland Allen 10m 59s

Did you have any formal process for deciding whether or not an idea was good, or it was just intuition? You know, "I don't like the sound of this. I don't want to spend my life doing this."

Ben Orenstein 11m 7s

I wouldn't say it was a formalized process. It was mostly intuition and then also just the shape of the business, which is, I wanted to sell software. I didn't really want to do consulting. I really, really wanted it to be something I could sell to my existing audience. I think that was very important and we can talk about why. But I think that's a huge component of our success so far. Those are sort of the big pieces.

Courtland Allen 11m 28s

Yeah. Let's talk about this because this is a very common topic of conversation. Should you build an audience before you start your business? Should you have a bunch of subscribers to your mailing list? Should you have a following on your blog or on Twitter? And even if you do somehow have an audience, how are you going to successfully sell what you're building to that audience? I talked to Mike Taber, one of the founders of MicroConf, on the podcast last year and he had a pretty big audience from MicroConf, from his blog about business tactics and strategies, and then he built and launched a product that was completely outside the realm of his audience. It was an email follow-up software for salespeople or consultants, and none of his audience wanted to buy it. So, I think it's great that you decided to have that constraint, that you're only going to work on something that your current audience would care about.

Ben Orenstein 12m 17s

So earlier I said – I gave one piece of advice, which is, if you want to do this someday, start saving money. That's part of it. I would say as important, maybe more important, actually, given the increase in funding options these days, is start building up an audience. That's the cynical take on it. Build an audience. I feel a better way to think about this is, be useful on the internet, which is a phrase I stole from my buddy, Adam Wathan, who does this better than almost anyone. It's just – how can you be useful? How can you be helpful? How can you put out good things in the world? It's less about how many email subscribers do you have or how many Twitter followers? And more like, how many people have seen you do good things and gotten value from it? In the early days of Tuple, we had people say, “I will pay you several hundred dollars just to support what you're doing because I've gotten so much value from you over the years. I don't even need what you're selling. I just want to support what you're doing here.” And that's pretty useful, it turns out.

Courtland Allen 13m 16s

Be helpful on the Internet. How do you do that? How did you do that specifically?

Ben Orenstein 13m 20s

Yeah, I worked at Thoughtbot for many years. A core part of Thoughtbot’s culture rubbed off on me, which is, I would say that ‘be useful’ thing is embedded deeply there. So, we will be at stand up (ph) and someone would say, “Oh, yesterday I learned that PostgreSQL something something.” And someone would go, “Oh that should be a blog post.” And there was just that – the strong undercurrent of recommendations to share stuff. So, lots of blog posts, lots of conference talks. Recording videos, just being helpful and giving back to the community. For me, that took the shape of conference talks. I decided I loved speaking. I tried it a couple of times. I really enjoyed it. So, I gave a lot of talks all over the world, which was amazing because, first of all, I got to travel a bunch with Thoughtbot paying for it.

I got to grow my own reputation and I got to build a group of people who had seen me do useful things. And there are talks I gave back in like 2012 that people still email me about today. Like, “Hey, I just watched that talk you gave about this thing.” And it's these dividends that are still paying to me. It's amazing.

Courtland Allen 14m 23s

This reminds me of the marshmallow test. It's where they give kids a marshmallow and say, “Hey, you can eat this marshmallow now or you can wait 20 minutes and we'll come back and give you a second marshmallow.” And half the kids eat the marshmallow and the other half wait. Supposedly the kids who wait and get two marshmallows have better career trajectories and make more money over time, etc. It sounds like what you're saying is the same, but for business. If you can be farsighted enough to do things that help others in the short term, that provide value, then it'll pay dividends for your business in the long-term.

Ben Orenstein 14m 56s

Exactly. And the great thing is, to me, I was eating the marshmallows the whole time. Giving a talk is really fun for me personally. I enjoy it. Recording my podcast is really fun. It's not hard work for me. I don't – it's not a sacrifice. To me, I feel like I'm eating the marshmallow and getting two later. And life is just great. I would encourage people to try to find something like that. For me, writing a blog post every week would be a chore. That does not sound fun for me. That would be a thing I would have to make myself do. I'd be like, “You're doing this thing because you know it's going to be good in the long term.” Recording a podcast does not feel like that for me. So maybe that's the opposite for you. Maybe it's something entirely different. Maybe you want to make a Vlog. I'm not sure. But if you can find a thing that it doesn't feel like that much work that's going to be – the sustainability matters so much more than perfection. It's all about how long can you adhere to this?

Courtland Allen 15m 46s

It's the number one reason businesses fail. People quit. It's because they're doing something they don't like and it's not worth it anymore. Or maybe it's because they ran out of money. If you can prevent yourself from quitting, you can make it hard to quit. If you save up enough money, if you do things that you like, you're much more likely to stick with it. And if you stick with it, you're more likely to succeed.

Ben Orenstein 16m 2s

One hundred percent. These two things that I was doing, saving money and being useful in building an audience, I didn't really know what they were for. They had some immediate benefits, but mostly I was just, I'm just doing this, and I don't know why I'm putting this cash in this account. I don't know what I'm going to want to spend this on someday. I don't know exactly why I want a bunch of Twitter followers, why this will be useful. But it's just turned out like, oh, hey, I'm making a company that sells to developers, this is going to be really great. I have all these people on an email list, and I have Twitter followers and things like that. And it was great to have been like, past me did current me a real solid by working on this over the years.

Courtland Allen 16m 42s

So one of the things that stands out to me about your story is that you had all the skills to really get this thing started by yourself. You are a software engineer, you built up an audience, you had marketing chops, you're not afraid of public speaking, and yet you decided to work with your co-founders. Why not start this as a solo founder?

Ben Orenstein 17m 0s

I am very extroverted. I'm very much a team player. When I quit Thoughtbot I didn't know what I was going to do. The first thing I did was I made a course, an educational course, about how to maintain slightly larger Rails applications. And the course did pretty well financially, but I did not enjoy it at all. Working by myself was just horrible. That, to me, was like torture. I don't do well if I'm not around people a lot.

Courtland Allen 17m 29s

What's the best part about working with other people? Is it just the day-to-day interactions and conversation, the shared wins? What do you find so magnetic about it?

Ben Orenstein 17m 38s

I never really dove into that. Some of it is that I have really high natural empathy, so this could be kind of a bummer sometimes. If I feel like I have hurt somebody or wronged them, it really messes me up. But the opposite of that is true, too. If I can do something cool for my teammates or make the company more successful, I feel extra good about it. Whereas if I sign up 10 new trials this week, I'm like, “Cool, that's great,” but the fact that I know that I'm helping row this boat that the three of us are in, it feels a lot better to me.

Courtland Allen 18m 11s

Yeah. Earlier you were saying that one of the reasons why you thought it'd be fun to start a startup was that you just like being on the steep part of the learning curve. You like having rapid progress every day. You like getting that positive feedback. And I think having a co-founder is kind of a hack for doing that. Even before you launch, even before you have any customers, before you have any sources of external feedback, your co-founder can look at what you're doing behind the scenes and be like “High five, Ben. Congratulations for doing that thing.” Whereas if you're by yourself, it really can be isolating, you can go for a long time without getting any feedback from anybody.

Ben Orenstein 18m 41s

Yeah. I found even success depressing when I was by myself. It was just too hollow. It didn't work for me.

Courtland Allen 18m 47s

All right, so you're the opposite of me. I'm an introvert. I need my alone time. I started Indie Hackers by myself, but that meant that I had to launch pretty quickly so I could get that feedback. With Indie Hackers I went from idea to launch in about three weeks. With Tuple, you and your co-founders took eight months, I think, from idea lunch. Is that right?

Ben Orenstein 19m 3s

That's about right. Yeah. We're about one-year old right now. That's about right.

Courtland Allen 19m 10s

I want to walk through the story of what happened in those eight months because there's a lot. You guys were coding, you were talking to users, you were doing presales, and even before that you had to all agreed to work on Tuple over all the other ideas on your idea list. How'd you decide to work on this particular idea?

Ben Orenstein 19m 28s

It had the characteristics that I wanted where it was software for sure and was something that would be useful to my current audience. But I would say we were kind of at – and it also had this compelling story. Which is, there was this great app for this called Screenhero. And then, mean old Slack came along and bought it. And ostensibly rolled it into their product, but not really, and then shut it down and no one could use it. There's this awesome narrative of, “And we, the brave little startup, are coming along to fight back against Slack and bring back this awesome remote pairing tool.” That was kind of nice, too. But I would say we were basically like 80%. Joel and I had a meeting at a coffee shop, and it was the, “Are we going to do this?” meeting. And it was – we walked out of that thinking, probably yes, it seems like yes. But we weren't quite at 100% and so I reached out to actually one of the co-founders of Screenhero and said, “Hey, I'm thinking about starting a company that would be the spiritual successor to Screenhero because I used it and loved it and I miss it.” “Could I buy an hour of your time, at whatever you think is reasonable, to pick your brain about whether or not this might be a good idea?” And he said, “Yeah, absolutely.” And by the way, didn't charge us anything, which is what always happens when you do that trick.

Courtland Allen 20m 46s

Oh, man.

Ben Orenstein Yeah. That's one of the best –.

Courtland Allen 20m 49s

I would have been like, yeah, $2,000.

Ben Orenstein 20m 53s

I would have paid it. That would have been worth it. Because, on that call he said, “Yeah, you should absolutely do this. I think there's totally still a market here. You're capable of doing it, just go for it.”

Courtland Allen 21m 5s

Is that what you expected to hear?

Ben Orenstein 21m 8s

I don’t know what I expected. I DM’d him this and he was like, “Oh yeah, there's definitely need here, let's definitely talk”. The initial response was very positive. When he just followed up with that, it was more positive than I was expecting. But that was when we went from like 80% to like a 100%. It's like, “We're doing it. We have to take a crack at this.”

Courtland Allen 21m 26s

All right, so you're all in at this point. You're definitely going to work on this idea. You and Joel have quit your jobs by this point. You brought on Spencer who has savings as well. What's the first thing you guys do to make this a real business?

Ben Orenstein The first thing that we did was Spencer and Joel started working on a prototype. So, our app is fairly complicated, of all the products I've worked on, usually the risk is not in technical execution. It's more like, “This is a Rails app and we're going to do form stuff and stick data in a database and it's a cred (ph) app.” This was very much not a cred app. This is real time, low latency video streaming. And that was a core part of our value proposition, which is “We think if we do this thing right, we can make remote control and remote screen sharing much faster and more pleasant than what we have right now in the market.” Not only do we have to make it work, we have to make it better than what most people are providing. Spencer and Joel got to work on a prototype and since the whole world of real time video streaming is complicated, they started with very basic stuff. We're not going to launch this to anyone. We just want to figure out the pieces and what this domain looks like.

Courtland Allen 22m 27s

That's pretty scary because you guys are burning through your savings building this technically difficult app with no real short-term plan to sell to anybody. Where are you concerned about that?

Ben Orenstein 22m 36s

Very much so, yeah. I thought that was probably our biggest risk factor in the beginning. So, while they were doing that, I was off pre-selling this product to make sure that the risk of, “No one wants this,” wasn't there. And I quickly discovered that was not going to be the problem. I pre-sold about $8,000 of this app before it even existed. It was like, “Clearly the dream is sellable if we can make a thing that is the dream.” That part is actually very scary.

Courtland Allen 23m 5s

You're the exact inverse of 99% of the founders that I talk to who are pretty sure they can build what they have in mind. No clue if anyone will want it, to agree to pay. What was the presale process like for you? How did you find people? How did you approach them? And how did you convince them to agree to pay for an app that didn't exist yet?

Ben Orenstein 23m 23s

So I was helped very much by the narrative that already existed and the context that was already there. So, a lot of people knew Screenhero and used it. My pitch was basically, “Hey, did you ever use Screenhero?” And like, “Oh yeah.” “Remember when Slack shut that down?” Like, “Oh yeah, that sucked.” It’s like, “Yeah, we're gonna try to make that.” And they go, “Oh my God, that'd be amazing.” And that was basically the whole sales pitch.

Courtland Allen 23m 46s

It's cool because we talk about idea validation. How do you prove that anybody will like your idea before you invest a bunch of time into building it, in a vacuum where you're building a totally new product that people haven't seen before? It's a lot of work. You've got to put your ear to the ground. You got to talk to people, you gotta try selling it. You've got to see what they're going to say. It's just a lot of proving to do. But the alternative approach is if you build something that people are already kind of using or that they've used in the past and paid for, in your case, you're building a better version, a new version of Screenhero, which is no longer available. In my case with Indie Hackers, I could see that people were already reading interviews like the ones that I put out, so I just made a slightly better version. We shortcutted validation. We already knew there was demand for this in the world and so we didn't have to go about proving it from scratch on our own.

Ben Orenstein 24m 31s

Exactly. So, I knew people loved Screenhero. I love Screenhero and I knew that what was out there was not as good as it was. It was like, “There's just this very clear gap in the market that used to be addressed and that is not now.” And when I look at the tools that people have in its place, they are not very good. And so, it felt pretty – like a short jump for me.

Courtland Allen 24m 52s

You guys had Screenhero as your product roadmap. In a sense you could just copy what Screenhero did, but did any of these early sales conversations you had with customers actually change your roadmap?

Ben Orenstein 25m 5s

Not really, honestly. We changed what we were doing a lot, but a lot of it was not based on customer feedback. It was more things we were bumping into and decisions we've made along the way. Thinking of ourselves as like a spiritual successor to Screenhero helped a lot, but it also hurt us in some ways where there were things that Screenhero did, that we assumed we would have to do. We would have to have an MVP (ph) that turned out to be a ton of work and also totally not true. It was mostly a help, but occasionally messed us up, too.

Courtland Allen 25m 34s

Okay, so you're out talking to customers, they're giving you feedback. Meanwhile, your co-founders are building a version one, I presume, of your app. You said it was never really intended to be put in front of customers. How did you guys make the switch into building something that was?

Ben Orenstein 25m 48s

So there were actually – the version of Tuple that we launched with was, I believe, the third complete rewrite of the app. So, version one was very much just like, let's understand the world of video streaming and audio and all that and remote control. Because they're just like the whole – it was just such a giant technical task that I was like, “Let's just build a thing fully knowing we're going to throw it away and just kind of get our heads around what this might look like.” Version one was built in Electron, which is this wrapper for web applications that you can run on the desktop. And Electron is great for prototyping, but it is, unfortunately, fairly slow and uses a lot of system resources. We knew that to deliver – at the end of the day, the value prop we want to deliver on, was like, low CPU use, low RAM use, blazingly fast. Wrapping this thing in a fairly slow, fairly bloated wrapper was fine for just understanding how this whole – all these pieces fit together. But it was clearly not something we could launch with.

Courtland Allen 26m 51s

Man, I'm getting stressed just hearing this. It's just so much code that you're writing. So much extra work just to build the product. That's not supposed to be the hard part. But luckily, you can do the sales part. You could do the marketing part and find customers while your co-founders worked on this.

Ben Orenstein 27m 6s

I was stressed too, to be clear. This was the scary part about this business. Normally, it's like what you said, it’s the opposite. But for me it was like, I know that when I tell people about beautiful, low latency screensharing they're excited about it and they'll even pay us money. I do not know that we can build this. Even going up into our launch, there were just these giant doubts in my mind. Is this fast enough? Is it good enough? Can we make it fast enough? If this were doable, why hasn't Slack had done it already? Why isn't this better? Is it really just this tiny team of the three of us are going to improve on the state of the art versus these enormous companies? How could this be true? So, it was scary.

Courtland Allen 27m 47s

I talked to a lot of founders who have ideas they’re excited about working on and I think one of the things I find myself saying very frequently recently is that a product idea is not a business idea. You can have an idea for a product and that's only one part of your business. You also have to think about the market, right? Who is going to use this? What do they value? You need to think about distribution. How are you actually going to get this product in the hands of your customers? Because you could build the best restaurant in the world, but it's the middle of the Sahara Desert no one's going to eat there. And then you have pricing, which sort of affects all of the above. Your pricing model controls what you can build, how you distribute it, who's going to pay for it, etc. We've talked a lot about the product that you guys built based on Screenhero. And we've talked a lot about the market. These are people who knew what Screenhero was, who really just wanted it back. But we haven't talked very much about distribution and pricing. So, let's start with pricing. How does you know what to charge for Tuple?

Ben Orenstein 28m 39s

Well, I knew exactly what to charge by testing every possible pricing scheme under the sun. I had no idea. And I think that's the right way to go about pricing, just test a ton of things. And this is definitely something I developed, during my time at Thoughtbot. In the beginning I was selling vaporware because we were – Joel and Spencer were cranking away on it, but it definitely was not a product. I would go to people and pitch them on this wonderful vision of the future. They'd be like, “That sounds great.” And I'm like, “Great. So, we're looking for – I'm looking for some people that are rare right now. So, I'm looking for people that want this badly enough that they're willing to put some money down, even though you can't try it yet.” And that you're someone that's willing to support the vision and really wants this thing to exist in the world. I'm going to ask you to prepay for a whole year and it's gonna – I'm gonna give you access. Once we launch, you'll have access for the whole Alpha, which will be some number of months and then a year after that. And they’d be like, “Okay, cool, what's that cost?” And then I would make up a number. The first number I threw out was like $149 a year. The first person paid that and then with every – just about every subsequent person, I would walk it up and say like, “Oh, it's $200 per person per year. $300, $500, $800 and just throw out different numbers and just to see what worked. And that was a really incredibly useful thing, because as it turns out there's just a huge range of willingness to pay across different kinds of companies and different kinds of people. Once we launched, I kept testing – I'm still testing pricing, honestly. I think I'm the closest I've ever been to settling on a price for at least the next quarter. But testing pricing and just even little tweaks about the trial and how much the trial – how long the trial is and whether or not it's free and things like that, I think have a huge impact on your business. I think it's – it can be a huge mistake to not just always be moving those things around and seeing what happens.

Courtland Allen 30m 29s

What are some of the things you learned from testing pricing? One of the most common mantras is to charge more.

Ben Orenstein 30m 34s

Yes.

Courtland Allen 30m 34s

Did you find that charging more ever hit some sort of limit? Did you find that it was always better to charge more?

Ben Orenstein 30m 39s

It's a very nuanced question, I think. I think I would've been more – clearly charge more is not always right. Otherwise your price would just effectively become infinite. So, there’s some number at which point you shouldn't charge more. The thing that I realized is that willingness to pay varies a lot. So, if you want to extract the maximum possible dollars per customer, there are fewer customers that are willing to pay that. There were people that would pay us a lot per user per year in advance, but there just weren't that many of them. So, I actually ended up dropping our pricing below – a good bit below the maximum we ever charged because I wanted more customers, I wanted more feedback. I was like, “Yeah, we could make a really nice business if we get 50 customers at this. But I think I'd rather actually have 200 or 300 just because we'll have more word of mouth and a little bit more momentum and people talking about it and more feedback, most importantly.” At this phase, I'm less concerned with optimizing like, “What's the revenue in May?” And more like, “Do we have good systems in place to get feedback from our customers to make sure that we are not just building the right thing today, but we keep building the right thing.”

Courtland Allen 31m 43s

That makes so much sense. And I think it's one of the things that a lot of people don't realize that pricing can affect. People think, “Oh, price is literally just the price that I charge.” That's pretty much it. But actually, pricing is everything. Pricing is how long it takes you to get to profitability. Is going to take you two years? Are you going to charge 10 times more and it's gonna take you two or three months? Pricing is how many customers are in your market. Pricing is what kind of customers can even afford you. It's who you're going to be interacting with for the rest of your business's life cycle. Pricing is whether or not you can afford to hire salespeople to sell your product or whether or not you have to rely on mass marketing channels. And this is something we haven't even really gotten to. We've talked a little bit about how you've reached customers, primarily through what seems like one on one sales calls. What other channels have you use to reach customers with Tuple?

Ben Orenstein 32m 27s

My answer to this like makes me slightly uncomfortable. I know the right answer is I'm supposed to be testing a bunch of channels and getting our marketing engine going and all that. We’re not. Just about all of our customers find us through Twitter or podcasts. And that's about it. One thing we do – this is another tip I would have for people is, ask people to do things for you. Especially if you've built up some goodwill in the past. If you sign up for our mailing list, after you sign up, you confirm your email, we say thank you so much for signing up. We're going to get in touch with you when Tuple is ready for you to try. Hey, by the way, we're a bootstrap team of three people. If you would share a link to this page on Twitter, that'd be super helpful for us. And there's a tweet button on it. And a ton of people do that. They even just take the default tweet text and so I know they're just literally clicking on that button and hitting share. We get dozens of these a week and people finding us through those. It's like if you built up a little bit of goodwill or maybe if not, if you just have a story that you think people will resonate with, give it a shot.

Courtland Allen 33m 28s

Oh, man, I'm going to steal that. I got to start asking people to do that in my intro email to Indie Hackers or something.

Ben Orenstein 33m 33s

Oh, it's so good. It works crazy well and it's just free. It gives you that viral component.

Courtland Allen 33m 39s

Yeah. You guys are super personal in everything you do. I was checking out your homepage and it's not – you have no illusion of trying to pretend to be this 5,000-person, super-professional company. It's very obvious. It's three guys. Like half of your homepage is kind of a jokey FAQ about you guys personally.

Ben Orenstein 33m 57s

Yes. Yeah and that's very intentional. I think that's actually one of your advantages as a small startup. I make it very clear. When we email our customers, our signatures have “I'm Ben, I'm one of the co-founders.” You're dealing with someone who's working on this intimately. There's just no filter between the people that are building it and everyone else. And I think people like the journey. So many people that have become our customers have started off as listeners to my podcast and followed for a while. “Hey, I'm working remotely now. I can use Tuple. Can I get in there?” And by sharing as much as I can, they feel kind of invested and they are more excited. I think people like to buy from people. They don't want to just buy from a faceless company they have no connection to. It feels better to spend your money with someone that you know.

Courtland Allen 34m 45s

There's not enough written about how being personal and how having a story attached to what you're doing can really affect people. I was watching Childish Gambino, he's an artist, he was talking about a song. And I'd never heard of the song before. I didn't particularly care about it but he just kept talking about the story of the song, how it was written and how it was revised and then so-and-so covered it and it was so great but someone else covered it and it was bad and it got changed and by the end of him telling the story of the song, I just wanted to listen to the song. That's all I cared about was, what is the song? But if he hadn't told that story, I wouldn't have any desire to listen to it whatsoever.

Ben Orenstein 35m 19s

Totally. I think our brains are super wired for stories. One of my conference speaking tips is tell a story or two. It's a great opener, I think. If you just start a conference talk and say, “So three years ago I got this really terrible phone call.” Everyone's like, “Whoa, what?” And you have everybody's attention instantly. We're just primed for that. I think everyone goes back to kindergarten mode where you're sitting around in a circle and listen to the story. It just works really well.

Courtland Allen 35m 42s

Yeah. I liked that you said you felt bad about not doing some of the things you should be doing around distribution channels. Testing every single market, etc., etc. I feel bad about the same thing. I don't think anyone – I work at Stripe, Stripe’s a big company. I think internally at Stripe we feel bad about things that we should be doing that we haven't gotten to yet. What are some of the things you look forward to doing that you're not doing quite yet?

Ben Orenstein 36m 6s

I'm intrigued by the idea of doing fun, interesting things at conferences. So, I have some friends that work at Honeybadger, which would – by the way, they'd be good guests. There are definitely an Indie bootstrapped, exception monitoring service. And one thing they did that I'm just totally gonna rip off wholesale because it's an awesome idea. They will sometimes sponsor a bus to take people to a good venue to get food. It's they like when Rails Conf – Rails Confs was in some city that had an In and Out, but the In and Out was three miles from the venue. And so, they just rented a bus and bought people's burgers and were unofficial sponsors of the conference just by having this fun little event. I'm intrigued by the idea of doing some fun stuff like that.

Courtland Allen 36m 46s

That's one of the cool things about running a company is you can do whatever you want. There's no rules. You can take people out to eat. You can take people to your acapella concerts, you can do whatever you want.

Ben Orenstein 36m 54s

Yeah, exactly. That's just more along that same line of putting your personality in your business and making it sort of a personal story. I think it works on a bunch of levels.

Courtland Allen 37m 7s

Let's talk about this process of you guys transitioning from this super-private beta, under development company to January, you guys finally making Tuple a live product. Did you have any sort of big launch? What was your plan there?

Ben Orenstein 37m 21s

Well, actually to be clear, we're still in early access. You can't just sign up. You still have to go through me to get into the product. That will change someday. But we launched to our alpha customers January 7th. So that was the people who had prepaid and there was about, I think, something like 10 teams. That was an amazing combination of scary and exciting, I would say. Honestly, the day before I was like, “Maybe we should push this back a week or two. The product is so shaky right now.” And we technically hit the deadline in that we launched on time, but it was just classic MVP. A lot of duct tape and the happiest of happy paths worked. And if you veered from that at all, you were going to – the app was going to crash, like hard crash.

Courtland Allen 38m 11s

It's tough because you've got to figure out in the early days, what do we absolutely need to have in order to launch to people? What can we put off? Otherwise, you’re going to be building for 10 years. You’re never going to release. How did you guys make those decisions?

Ben Orenstein 38m 22s

Well, we screwed them up all over the place. So, we were convinced – so Screenhero had this great feature which was dual mouse cursors for both people on the call and we're like, “Dual mouse cursors is great. We’ve got to have dual mouse cursors.” And we spent hundreds of hours of development time on dual mouse cursors. The problem is dual mouse cursors is always a hack. There's just no way to do – the operating system is like, “There is one mouse cursor and you will not convince me that there is two.” So, it was just hacks on hacks on hacks to make it feel like there's two cursors. And you just have so many edge cases and so many bugs. We launched with it and there were just tons of problems with it. A week or two in I was like, “You know what? What if we just like did a one-click handoff? One person can control the mouse at a time. You just click once and suddenly you have control.” And Spencer was like, “I could get that done in two hours”. I was like, “Great, let's do that.” We did that, and we disabled the dual mouse cursors and we get almost zero complaints about missing the dual mouse cursors.

Courtland Allen 39m 20s

Nice. What are some of the things that changed when you guys finally launched? Going from nobody paying you, really, to people paying you and suddenly you have to support this product. What was going through your head January 7th and the few weeks after that?

Ben Orenstein 39m 36s

Well, I was really nervous about launching because every time I used the app, I was like, “Man, there's so many problems.” And there were lots of problems. There were lots of issues when we launched. But what surprised me was how forgiving our early customers were. It's like on our early calls, I would demo the app and it would crash. And they would still be like, “This is awesome. It's a bummer that it crashed. I'm sure you'll figure that out. I love that you've done x, y, z.” And they were just excited and focused on the positives. And that really shocked me because I was expecting people to just be incredibly tough or ruthless. And instead they were very understanding. And I think part of it is just that they were developers, too. I'd be like, “Oh man, yeah, this is really tough because this thing is like a C++ and multithreaded. So, it's actually really hard to know if we have a lock on the right thread.” And they're like, “Oh yeah, that sounds really hard. I totally get it.” And they would just be like really great about it. And that has actually continued and been a really pleasant surprise.

Courtland Allen 40m 34s

It’s cool building any sort of business where the people who you're selling to are doing the same thing that you're doing. I have the same thing with Indie Hackers. The forum is full of people who are trying to start a business, who are trying to make these difficult decisions themselves. Everyone's really nice to me, they’re really nice to each other. I've had the opposite experience in previous businesses, man, where I get angry customer emails about bugs and issues. It's such a difference in your quality of life as a founder to have nice customers who understand what you're going through.

Ben Orenstein 41m 2s

It's so is, yeah. And I'm so glad I sell to developers because I understand them. We understand each other, I guess. We have this instant rapport and that just makes life feel better. I'm happy to keep serving this audience for a long time.

Courtland Allen 41m 16s

So do you remember what your revenue was like month one after launching?

Ben Orenstein 41m 21s

Revenue in month one? Probably almost nothing. I was continually selling the product. I got that Alpha group together, but then I was still trying to – I can just go look. Let's go, let's answer this.

Courtland Allen 41m 35s

Yeah, let's check it out.

Ben Orenstein 41m 39s

January revenue – net revenue was $1,500.

Courtland Allen 41m 43s

Fifteen hundred dollars, three co-founders. Pretty far cry away from ramen profitability. But you guys are still living off your savings. What's your revenue at now?

Ben Orenstein 41m 52s

So we're on pace to do over 20k this month.

Courtland Allen 41m 55s

Wow, that's huge. It's been four months since January.

Ben Orenstein 41m 59s

Yeah, four months. Yep.

Courtland Allen 42m 1s

Fifteen hundred to 20K. What are some of the biggest things you guys have done to make such a quick leap so fast?

Ben Orenstein 42m 8s

The answer is not going to make anybody happy, I think. We built up this email list as you do. One of the first things we got together was a landing page, which says, “Hey, we're making a thing.” That email list has close to 5,000 people on it now. I've just been steadily driving people to that constantly. The reason for our – basically a ton of our trials these days come from the mailing list. I'll just pull off another 500 people and email them and say, “Hey, your invites up. Here we go. Do you want to use it?” We’re cashing in stuff – we're spending our savings of email subscribers that had been built up over the last year.

Courtland Allen 42m 45s

Oh cool. You're emailing small subsections of an email list. You're not doing one big, everybody's in. Why do it that way?

Ben Orenstein 42m 52s

Correct. I have been – because something always goes wrong. There's a bunch of reasons. One is, man, if you just like do it all at once, you can't do it again. It's like you've used it. If you screw something up or if there's a link that's wrong or the thing crashes, it's just like, “Wow, I've just – now I'm really hosed.” I would say part of our DNA, I think we've been saying from the beginning, we don't have to be in a rush. We want to get to ramen quickly because we don't want to die. But we don't need to be huge. There's no VC pressure, any of that. Let's go in a sustainable pace. We do that with basically everything. We're launching a major new feature this week and so we're rolling it out to a small set of people behind a feature flag. We just want to make sure that we do things in a slow, sensible way. Also, if you launched a cohorts you can change the price every time you do it.

Courtland Allen 43m 43s

So you guys are still tweaking pricing. You're still trying to figure out what it's going to be?

Ben Orenstein 43m 46s

Not much anymore. It's pretty well dialed. People actually joke, people will email me back and be like, “Am I in the high-price cohort of the low-price cohort on this one? Cause I talk about this on my podcast a lot. These days I mostly – I'm just offering the same price to everyone. But at the beginning I was very much testing different pricing levels. We still are iterating on things that are not quite price but pricing model. In the beginning – we charge per seat and at the beginning I would be talking to someone and they'd be like, “Yeah, I want to sign my team up.” And I'm like, “Okay, great. We charge x per seat. How many people do want to start with?” And they'd go, “Oh, I'm not really sure, let me go check. That was like a huge road bump in the sales process and often they would just disappear and then they would just never come back. A thing that we switched to that has been huge for us is we do $100 for your first month, regardless of how big your team is. There's no decision required. You need to put a card down and by default we're going to charge you per people, like for everyone that signs up that you want to keep going with. But it makes it really easy to get into the product and actually use it.

Courtland Allen 44m 48s

Such a consistent theme that I've found when talking to founders like yourself, that forcing people to talk to you personally, even if it's just over email or something, is such a great learning experience. You get this feedback that you would never get if you just had a pricing page up and people looked at it and then just left and didn't tell you why.

Ben Orenstein 45m 0s

Exactly. And you'd be like, my conversion rate to paid is 0.89%. People say it should be 1%. I wonder why that is. Good luck tracking that down. You're like, “Is that bad? Is that good? I don't know”. You wouldn't feel that pain of like, “Oh man, I'm losing a lot of people at this stage in the funnel.” I actually think that this is a very common failure mode for Dev-founded startups. I say the most common failure mode is not charging enough, or not testing pricing enough. Then also it's wanting to over automate. I'm pretty adamant that we only automate things that we're already doing manually that we feel confident about and feel good as a process. And then when it becomes annoying, we automate it.

Courtland Allen 45m 37s

Yeah. If you loop yourself out of the business, you're probably the most important part of your business, especially early on when you don't know why people want things. So, you can't really code yourself out of the process too early otherwise.

Ben Orenstein 45m 48s

Hundred percent. There is this beautiful idea –I want to build the fully automated thing, too. I want to be able to sit on the beach and have Tuple’s revenue go up. That's where I want to get to. But I'm trying to do it very slowly and piece by piece, where I feel like I understand how a certain thing is working and then automating that. But until a month ago, I was generating every invoice on Stripe and manually emailing it to somebody. Then when they paid it, I would go into the Rails console. I would do, team (dot) new and straight up build them their thing on the backend. And we have only recently started automating these pieces because I’m doing so many of these per month that it’s annoying. But there have been things where at first, we’re like, “Oh, we're definitely going to need to automate this.” And then three months later we've barely done it. I was like, “Oh, actually we don't need to automate that.” We're avoiding a real cost there.

Courtland Allen 46m 39s

I'm curious how you came to these learnings and these realizations because like you said, the intuitive thing, especially as a developer, is that you've got to automate stuff. And even when you're not automating it and it's taking up all your time every week, it just feels wrong. How did you come to know that actually it's the right thing to do, to talk to your customers? How did you learn any of this stuff?

Ben Orenstein 46m 58s

The way that just about everybody learns everything, which is by doing it and screwing it up lots of times. And then learning from my mistakes. Tuple is not my first business. I started a business inside of Thoughtbot. I have run other SaaS apps for Thoughtbot. I have gone on retreats with friends and launched small SaaS products in a matter of days and run those on the side as side projects. I have built info products multiple times and sold those. I've been trying to get people on the internet to give me money for a long time. I've been able to avoid a lot of missteps right now because I have made a lot of missteps already.

Courtland Allen 47m 34s

Give me an example of one of these things that you started where you perhaps made a lot of missteps.

Ben Orenstein 47m 38s

One example is, I was running a product at Thoughtbot called FormKeep, which was form end points as a service, which is, if you needed a place to like post a form to, to hold some data, from a mostly static website, you could spin up a whole server or you could just point at one of our specific end points and we'll capture that data for you and then forward it to Zapier and things like that. Like a classic developer-created tool, we were dramatically undercharging for it. The original pricing model for FormKeep was “pay what you want,” which is $0. Well, there was a scale, so you had to pay at least one. There's a slider from one to like a hundred or something. And guess what price of both people want to pay when given that option?

Courtland Allen 48m 21s

A dollar.

Ben Orenstein 48m 22s

Yeah, a dollar. Exactly. We had a whole bunch of customers at a dollar and eventually I scrapped that. When I took over the product. I was like, “No, no, we have to get rid of this and charge real prices.” But even then, the prices I picked were pretty low. One day I noticed that Uber had signed up and was sending like tens of thousands of submissions to the end point that they had created. I was like, “Holy crap, that's amazing. Uber's a customer. Hey, what plan are they on?” And it's like $19 a month. Oh No. So, I went, and I looked it up and I was like, “Uber is losing like $2 billion a year right now and I am $19, if that. I think our pricing might be wrong.” Learning how to charge more is partly because I've charged the wrong amount a lot of times.

Courtland Allen 49m 8s

Well, that's another situation where if Uber had called you on the phone or sent you an email, you'd be like, “Holy shit, it's Uber. The price is $20,000 a month.” And they would not have blinked.

Ben Orenstein 49m 18s

Exactly. There's a lot of value to that enterprise call us plan.

Courtland Allen 49m 24s

Let's stick to this topic of learning. One of the things that I think makes you particularly interesting as a founder, is that the prototypical startup founder is this Bill Gates, Mark Zuckerbergesque character who has rich parents and just aced everything in high school. They were a genius programmer. They went to Harvard. Just breezed on through and then started some world-changing, billion-dollar company. That's very much not your story. That's not the story for the vast majority of people. Give us a little bit about your background and how you got to the point where you became a developer and became confident enough to be a founder.

Ben Orenstein 49m 58s

I do actually share a little bit of past with Mark and Bill in that, I also did not have a college degree. Although, they left voluntarily. I was actually kicked out of college due to academic deficiency. I was someone that did okay in high school, mostly by not being super challenged. I could coast a fair amount. I got to college and it got way harder and I had no self-discipline and no study skills. Suddenly the courses were much, much more intense. I basically train wrecked. I failed my way through several years of school, just barely scraping by. Eventually my GPA got low enough that the university was like, “You have to take at least a semester off.” And I was like, “I should probably take more than that.” I moved home and I got a job as a bartender at the Olive Garden. That was my first entrance to the workforce as an “adult.” And that triggered a good period of self-reflection, as you might imagine. There's nothing like a healthy dose of shame to really force some looking at yourself. And I came to the pretty fast conclusion that, look, this is not how I wanted my life to go. I just started working on getting my act together. I think, honestly, just facing consequences in a serious way for the first time was really the trigger. I lived, actually, a pretty sheltered life. I had a really nice childhood and a childhood, very much sheltered from consequences and negative feedback, I guess. For the first time I couldn't run anymore. I couldn't talk my way out of it. It was just, “Nope, you got kicked out of school. You have a crappy job that you're not happy with.” And I was like, “Okay, I understand at a visceral level now that my actions have consequences. Let me start making some better actions.” I just literally started bending the curve in the right direction. After not very long as a bartender, I got a job as a server at a fine dining restaurant, which actually is a big step up, believe it or not. And then, fell back on some of my IT/computer skills to get a job as an IT consultant, driving around to different companies and taking care of their servers. And then that turned into an entry level programming gig and that turned into a better programming gig. And I just kept upgrading my job every year or so. And fighting my way into what I wanted, which was a really good programming job.

Courtland Allen 52m 29s

A lot of founders have anxiety about not being ready to start a startup. I hear this all the time, like, “I should – I want to start, but there's so much to learn. I'm not necessarily a developer yet or maybe I am, but I don't have the business skills.” What have you done besides just learning from the school of hard knocks? Do you read blog posts? Do you read books? How do you, I don't know, educate yourself as a founder?

Ben Orenstein 52m 49s

I'm in a weird spot right now where I want there to be really good resources for me that will tell me the right thing to do now that I have to make these difficult decisions. And the more I look for them and the more I actually run a company, the less confident I am that there exists this resource. I actually think there's just a lot of different ways to do this. You can try to do it in the way that somebody else does. And for a while it stressed me out because someone would be like, “Oh you need to know what your top three marketing channels are and you need to be constantly testing,” and I'm like, “Oh God, I'm not testing or iterating anything on the marketing side.” Pricing, sure. And I was stressed out because some blog posts told me I should do a thing and I'm totally not doing it. But things are working. We're solving a very complex problem here, which is like, “How do you make an engine that spits out money at the other end?” And there's a ton of different ways to make these engines and they can be shaped into a whole bunch of different configurations. I'm getting more and more to the point where I feel like I'm just going to figure this out as I go. And there's some smart people I like talking to. That's actually probably been the most helpful thing, is to actually have friends that run businesses and to bounce ideas off of them. And have a little bit of a mastermind. Or go to conferences like MicroConf and talk to other people doing it for ideas, but also rejecting those ideas when they don't feel right to me.

Courtland Allen 54m 15s

Yeah, I found the same thing, man. There's just no one right answer out there. And the harder you look, it's just – you're building a unique business. No one's ever built the exact business that you’ve built with the exact time with the exact customers. So, they're not going to know the answer because there's too many variables.

Ben Orenstein 54m 28s

Yup, 100%.

Courtland Allen 54m 30s

One of the cool things that you've done, though, that I think I also did to a degree and I think anyone can do, is to find an analog. Some sort of other company who's already done something similar to what you were doing and use that as training wheels in the earliest days of your company. You guys knew what to build because Screenhero was a thing that existed. For me with Indie Hackers, a lot of my early playbook was really based on this website, Nomad List. I copied what they did, like aggregating data in one place and then building a mailing list and then turning that into a community, etc. Do you have any companies that you look up to now that you're at this point where you guys are pretty much ramen profitable and you've – I don't want to say caught up to where Screenhero was, but you are certainly beyond the early days.

Ben Orenstein 55m 14s

Yes, there are a few companies I really admire. One is Wistia, which is a local company. They're out there just down the street from us and they're a video hosting company. And I think the thing I admire about them is that I feel like they've come to the same conclusion, which is you have to do things that feel right to you and run your business in a way that feels appropriate and makes you feel good and makes you have a good time doing it. I look up to them for having longevity and building a great product and having so much personality and everything. That’s the first thing that jumps to mind.

Courtland Allen 55m 46s

You have a lot of crossroads and you're going to come to pretty soon. You guys are at the point of ramen profitability. You're talking about building a business that lasts and staying happy, but there's all sorts of questions that come into that. Are you going to hire employees and try to grow as fast as possible? What direction are you going to take the product? How much money do you really need? How many hours should you be spending working? How do you grapple with some of those decisions and how do you talk through making them when you have co-founders who might disagree?

Ben Orenstein 56m 14s

We're pretty good at agreeing with each other, actually. It seems like we're pretty philosophically aligned, which is nice. We tried to make sure that was true. And fortunately, luckily, so far that has held true. I will say that it feels like our ambitions are subtly, maybe not so subtly, increasing as we hit different levels of success. In the beginning, two months ago I was just like, “We just got to get to 15k, so we don't die.” Because 15K for us, we can basically pay our rent and bills and whatnot, for the three of us. And it was just like, “That's all I want in the world.” And now it's like, “Okay, we're above that now what?” I was like, “Oh, now what, indeed. I don't know exactly.” I feel my aspiration lifting a bit, for sure. Where it's like, “Okay, it looks like the basic thing is going to work. What kind of company do we want to build?” We had said for a long time that we don't want to hire people and I think we don't want to hire quickly. I think we would rather biased towards small, but at the end of the day, if there are more people paddling the boat, the boat can go to all kinds of new places and go there faster. And that sounds kind of fun. A thing that people ask us for a lot right now is a Windows client or a Linux client. We're a Mac only. You could hire someone that is great in the Linux environment or is a Windows expert and then suddenly you have new expertise on the team, you can accomplish new things. I could see why you might want to do that.

Courtland Allen 57m 38s

Yeah. What about a work/life balance? Because I've seen you express some strong opinions about this. How many hours are you working on Tuple? How's that changed over time?

Ben Orenstein 57m 50s

I have no idea how to answer that question. So, if I am lying in bed from 9:00 PM to 11:00 PM and I'm just lying there looking at the ceiling and thinking about work, am I working?

Courtland Allen 58m 2s

I don't know, man.

Ben Orenstein 58m 4s

Exactly. I have no idea how many hours I’m working. I think about the business all the time. It's my favorite thing to think about. I spend more time thinking about it than almost anything. I don't know if that – if you consider that working or not. Who cares? In a way, how many hours a week do you work on the businesses is the least interesting question. How many hours do you spend at practice? Who cares? Are you winning the games? Are the games going well? Great. If you can practice 10 minutes a week and win the games, that's awesome. I'm not super interested in optimizing that, except for maybe just making sure it's the number I want it to be or that feels right. I worked – I put in some time on Sunday night because I wanted to ship this one feature that I've been hoping to do. And is it the most important feature for the business? No, but I felt like writing a little bit of code, and it made me happy to get it out the door. I spent some hours on that. And counting that time towards work time? Sure, yes. I was working, my fingers were on the keyboard, but I was just scratching my own itch at that point. So, I don't really know how to answer it, but to me it's the wrong question. The right question is, “Are you working a sustainable amount? Can you keep doing this for a long time? Can you marathon this pace?” I think that's really, really important. And then, do you feel generally fulfilled while you're doing it, or does it feel like a slog?

Courtland Allen 59m 19s

Well listen, man, it sounds like you’re on the right path. It sounds like it's not a slog. It feels great for you. You guys are killing it on the revenue growth side of things, and all of your problems seem to be the kind of problems the kind of problems that you want to have, deciding what kind of business you want to build.

Ben Orenstein 59m 33s

Well, I appreciate that. I feel extremely lucky. I'm having so much fun and it's working. It's amazing. I'm sure I would be giving a very different interview if we were still at $1500 a month. I would be feeling a ton of stress and kind of miserable. And like, “Building businesses sucks,” but so far everything seems to be working. I feel great. I'm having a super fun time.

Courtland Allen 59m 54s

I've had a lot of fun talking to you, Ben. Can you tell listeners a little bit more about where they can go to find you online and the things you're working on and learn more about Tuple?

Ben Orenstein 1h 0m 3s

Totally. So probably the best thing, given that you're a podcast listener, if you have room on your plate for another podcast, mine is called The Art of Product and if you like hearing people talk about building businesses, I have a co-host and we're both working on startups. Our podcast is almost like a mastermind where it’s the two of us chatting with each other, and thinking through problems, and sharing numbers, and just trying to get better. So, if that sort of thing sounds interesting, maybe check that out. I'm R-zero-zero-K on Twitter if you want some hot takes. And if you want to learn a little bit more about Tuple, I'm going to put together a special page for Indie Hackers listeners, which will be at Tuple.app/ih

Courtland Allen 1h 0m 39s

Cool. Thanks so much for coming on the show, Ben.

Ben Orenstein 1h 0m 42s

It was so fun. Thanks for having me.

Courtland Allen 1h 0m 49s

If you enjoyed listening to this conversation and you want a really easy way to support the podcast, why don't you head over to iTunes and leave us a quick rating or even a review. If you're looking for an easy way to get there, just go to IndieHackers.com/review and that should open up iTunes on your computer. I read pretty much all the reviews that you guys leave over there, and it really helps other people to discover the show, so your support is very much appreciated. In addition, if you are running your own internet business or if that's something you hope to do someday, you should join me and a whole bunch of other founders on the IndieHackers.com website. It's a great place to get feedback on pretty much any problem or question that you might have while running your business. If you listen to the show, you know that I am a huge proponent of getting help from other founders rather than trying to build your business all by yourself. So, you'll see me on the forum for sure as well as more than a handful of some of the guests that I've had in the podcast. If you're looking for inspiration, we've also got a huge directory full of hundreds of products built by other Indie Hackers, every one of which includes revenue numbers and some of the behind the scenes strategies for how they grew their products from nothing. As always, thanks so much for listening and I'll see you next time.