3x Growth, Dating, and Hiring a Coach for Everything with Ben Orenstein of Tuple

Courtland Allen: 0s

What's up, everybody? This is Courtland from indiehackers.com and you're listening to the Indie Hackers Podcast. More people than ever are building cool stuff online and making a lot of money in the process. On this show, I sit down with these indie hackers to discuss the ideas, the opportunities, and the strategies they're taking advantage of so the rest of us can do the same.

Alright. I'm here with Ben Orenstein, one of the co-founders of Tuple. Ben, how’s it going?

Ben Orenstein: 32s

Dude, it's going great. It's great to be back on the pod.

Courtland Allen: 34s

It's great to have you back. It's been a year and a half, two years. I wanted to have you on last year. And then I don't know what happened. A few small things like a global pandemic.

Yeah, things of that nature, but now you're back and I want to get people sort of a catch up as to who you are since it's been a year and a half. Maybe the best way to do this is to sort of retell the story you have on your website. I'm going to try telling it, you tell me what I get wrong.

Way back in the day, there's this app Screenhero and you could use it to call somebody and to share your screen with them. It was super good. It was fast. It was reliable. It's high quality, everybody loved it. In fact, it was so good that programmers would use it to collaborate and write code together in a pair.

Then the unthinkable happened. Slack bought Screenhero and shut it down. So, this amazing thing that existed in the world suddenly ceased to exist. That's where you came in, Ben. You were looking for a startup idea and you ended up making a modern, sleek Screenhero replacement called Tuple.

I think you were last on the pod in late 2019, you hadn't even launched yet, but you’d done a bunch of pre-sales. You had beta customers; you were doing something like $20,000 a month in revenue. That was a little bit over a year and a half ago. Since then, we've had a global pandemic. Remote work has become kind of like the new norm. Where are you at now in terms of Tuple’s progress?

Ben Orenstein: 1m 46s

Yeah, we're we' at like millions of dollars a year. COVID was crazy for us. The business more or less quadrupled in a month or two starting in March of 2020. Then the next couple of months were crazy, too. Basically, since then, they're not quite as crazy, but our growth rate is three X what it used to be. So, it’s been good for us, for sure.

Courtland Allen: 2m 4s

And how big is your team now? Cause it was just three of you in total when I talked to you.

Ben Orenstein: 2m 10s

Yeah, so I have two co-founders. So, it's just the three of us last time. Now, we are five full-timers and three part-timers.

Courtland Allen: 2m 17s

So I take it you're probably profitable unless you're paying everybody a very, very good salary.

Ben Orenstein: 2m 22s

Yeah. Yeah. Definitely. Definitely profitable.

Courtland Allen: 2m 24s

Cool. Well, that's awesome, man. Congratulations. I've talked to a few people recently who just had their businesses explode in the last year and COVID seems to play a role in all of them.

Ben Orenstein: 2m 36s

Totally. I mean, yeah, everything shifted so much. One of the reasons we picked Tuple as an idea was that we thought there would be more remote programmers every year. It just accelerated an insane pace where suddenly it was like guess what, everyone's a remote programmer.

Courtland Allen: 2m 51s

It’s pretty nice to build a business on a wave that's growing. It's pretty safe to predict there will be more software engineers in the future.

Even if everybody switches to no-code, they're probably going to collaborate over the internet and need some sort of pair programming tool. It's kind of like you're betting on almost a sure thing. When the market grows to some degree, I mean, you're not doing anything you're doing quite a lot, but you could do nothing and there would just be more customers there for you tomorrow.

Ben Orenstein: 3m 17s

It also helps with just thinking about competitors. It's like, okay. There are these people over here doing this and these people over here doing this. But also, every month there's more programmers and every month, you know, some go remote or work from home a bit more or something like that.

Courtland Allen: 3m 30s

Competitors are funny. It's one of these topics that I think a lot of us will say one thing in public when the reality is very different. Paul Graham actually tweeted, I don't know exactly. He said, it was basically something like when people say that they're flattered by competitors and copycats and this proves that there's a market, the reality is they're actually super annoyed by it cause copycats suck.

I read that tweet and was like, that's so true. Every time anyone copied Indie Hackers for anything I was working on, it was just like, this sucks. I'm already having a hard enough time with trying to grow this thing.

I don't need someone to rip it off my idea, taking my customers, et cetera, but I'll go in public and say this just proves that the market exists, and it lights a fuel. It's a fire under my butt that I'm gonna work even harder. It's kinda bullshit.

Ben Orenstein: 4m 10s

It is. Yeah, there's that unflappable magnanimous, you know, exterior persona, and then your real actual monkey mind that's mad and wants to get back at them.

Courtland Allen: 4m 22s

Exactly. But you, despite having, do you have any competitors? Are there any serious of challenges for Tuple?

Ben Orenstein: 4m 29s

So for a while, it didn't seem like anyone else was positioning themselves for the pair programming market, which is what we go after. So, we have built the whole app around the idea that it's for developers doing pairing.

It's not generic screen sharing, not generic video conferencing kind of stuff. There wasn't a lot of people in that space before. There are more now. It's, you know, it's happening, which is not shocking. This was to be expected, but you prefer if there weren’t, right. It'd be great. If it would be nice, like, yeah, we don't want that niche. That'd be the best, but, you know, I just find it very flattering, and it helps balance the architecture. So, I'm glad to see it.

Courtland Allen: 5m 1s

But you got quite a head start and you've got a very intentional positioning because like I was mentioning earlier, anybody could use this, even if I'm not a developer.

If I wanted to, you know, be a no-code person and collaborate with another no-coder, I could use Tuple, but you've very specifically said this is the best remote pair programming app, because programmers are better. That's what it says at the top of your homepage. It's means in a way you're excluding other people who might not be turned on by your messaging and you just don't care. It's worth it for you.

Ben Orenstein: 5m 29s

And also just the competitor thing. When people have used Tuple for a little bit, we asked them what they were using before and asked them if they like Tuple better as a little customer survey.

Interestingly, the people that I consider our competitors in terms of positioning similar to us and doing a similar thing, don't even show up on this list. Our competitors such that in the sense of apps that people have used before switching to Tuple from are basically Zoom, Slack Halls, Hangouts/Meet. That's it.

So, it's like, I'm aware. I'm hyper aware of everyone in the space, right? I'm like, oh, these guys are over here doing this. And these guys are over here, a little different because they have this angle on it.

Most people are just using Zoom. So, they try Tuple and are like, this is way better than zoom for pairing. And we're like, there we go. You're our customer.

Courtland Allen: 6m 13s

It's the same thing that happens to everybody who builds like a to do list app or productivity app and they're like, who's our competition. It always turns out that people are like, I use sticky notes. I'm using a notepad. I haven’t been using the high-tech competitors that everybody's afraid of.

So, do you feel that in any way being transparent about your numbers, like you didn't share your exact revenue numbers, but you're happy to go on podcasts and say that you're doing millions of revenue, that your revenue quadrupled.

Why do that if you have competitors and you have like, not necessarily the best feelings about the fact that these people exist?

Ben Orenstein: 6m 42s

I sorta don't buy the idea that just by talking about your revenue, you're going to create savvy competitors out of the air. Maybe at the margin there's someone who has three different ideas, and they listen to this podcast and they go, well, Tuple’s making millions, I'm going to do the one that's most like Tuple. Maybe, I guess.

If you can just hear me talk about this and then go create something better than Tuple and compete with us so effectively that we start to lose customers to you and our revenue goes down like, wow, like, damn, you're going to beat us anyway. You didn't need me to tell you that, hey, this is a good business to sell programming tools to programmers.

Courtland Allen: 7m 16s

That's funny you mentioned savvy competitors because you've got a podcast and your cohost Derrick Reimer has a company called Savvycal, and he's literally done this thing.

So, there's Calendly, which many of us use to sort of, I used to schedule this podcast call with you. I sent you the link. You pick a date that's free on my calendar, super simple. It's got a lot of issues. Everyone knows Calendly has issues, and everyone also knows that Calendly is crushing it because the founder would go on podcasts and talk about how many millions of dollars they're making.

It just seems from the surface to be a really simple app. So, Derrick came and built and he's one of these competitors nipping at their heels. He built Savvycal. I think he just hit what, $10,000 a month in revenue recently. He is a very savvy competitor. I don't know if he's going to crush, Calendly into the dust or anything like that, but he's certainly making a run for it.

Ben Orenstein: 8m 1s

That's the thing, but Derrick didn't start Savvycal because he thought Calendly was making a lot of money. He looked at Calendly and said and talked to customers of Calendly and found some of their dissatisfaction and said, I think there's space for a thing that does things a little bit differently here.

It wasn't just like, oh, they're making X million, I want some of that. It was like, I see a gap and I think I can execute well in this particular niche. Maybe I'm wrong. Maybe I'll come back on the podcast in a few years and say, well, Courtland, I never should've mentioned that because I inspired all these copycats that then went out and beat us and overcame our lead.

Courtland Allen: 8m 34s

Well, how do you feel now that you have this lead? I mean, I talk to a lot of people who obviously want to be where you are now. I think the last time I talked to you, you would have told me that you want to be where you are now. That probably would have seemed much more than a year and a half out.

Now that you're here, does it feel like you still have the fire to keep growing the business? Do you feel like you're settled down a little bit? You want to focus more on your personal life? What's going through your mind now?

Ben Orenstein: 8m 55s

Here's the thing that I've been realizing about the startup life or just having a company, which is everyone says like the highs are high and the lows are low. I think that's pretty true. The highs are higher, and the lows are lower than say having a job.

But also, there's this peculiar quirk in my brain, and I think a lot of people's brains, which is that as soon as I come down from the high, I don't want to lose any little bit of the high. Every time we hit a new high MRR mark, if we go down a thousand dollars, I'm like, ugh, that's the worst.

It hurts so much. Or we drop, you know, we have a big day and a big customer cancels and it hurts. Or even, we signed a big contract with the customer, but it was an unlimited deal and we're not getting expansion revenue from that anymore. Even though it's a huge contract, I still feel the loss of that.

So, it's just, it's hard to make yourself happy is one of the things I've realized with business success. It's not a good happiness regent.

Courtland Allen: 9m 49s

That makes sense. We are animals. We evolved in the wild. We really, really, really didn't like losing things. You know, you gathered a bunch of acorns. You better keep those acorns because you might starve to death.

Charlie Munger calls it a loss super deprival reaction syndrome. He has this funny name for it, but I think psychologists call it loss aversion. And it's this idea that people are much more, much sadder about losing a thousand dollars than they are happy about gaining a thousand dollars, which means you have this sort of a mindset switch as you become more successful or gain things that are important to you in life.

Or instead of kind of being the starry-eyed child, looking out into the world and saying, what do I want to do? What can I accomplish? You start thinking how do I keep all the stuff that I have and not lose any of it? Cause it's pretty fucking awesome.

Ben Orenstein: 10m 33s

Yeah, it's so irrational, too. I was talking to Joel, my co-founder about this the other day. I was like, well, what if revenue drops by this much? He was like, well, if revenue had just gotten to the point of that, the bottom of that drop, but it had done it slowly rather than going up and then down, if it had gone there directly, you would feel totally fine about it.

I was like, yeah, I would feel totally fine. It’s the fact that we went down from a higher number that makes me really upset now. It's just man. I guess the big lesson there is try good luck, good luck. But try not tying your happiness to how the business is doing. I mean, I have not had much success in that.

Honestly, I'm very tied to it. But I'm working on it. I'm meditating, trying to do my waking up app and try to be calm and stuff and make success.

Courtland Allen: 11m 14s

It's hard not to. It's something you're spending, it's your life's work, right. You're spending a great deal of your time and energy and effort on this. It's hard to say I care about this enough to spend all my time on it, but not enough to feel any negative feelings when things don't go well.

I think the trajectory of the change matters, too, because if you hit this revenue number a little bit more slowly, that actually is I think, better than hitting it and then reverting. Cause if you revert, that means the trajectory is now going down and you don't necessarily know where the bottom is.

So, part of that is kind of a fear it went down this month, but also will it keep going down if we like lost some spark? I think in your particular case, you have any apprehension about the fact that the pandemic is going to end in some form or fashion, right?

Everybody's getting vaccinated. Things are gonna go back to normal. People are going to work in the office. I just saw something today, Google's rapidly reopening their offices or something. A part of your tailwind has been the fact that we've had people working remote.

I could imagine that there might be some fear in the back of your mind, like maybe this won't last forever. Maybe the good times aren't here to stay and we're going to go back to some baseline level.

Ben Orenstein: 12m 15s

Yeah. That could certainly happen. I'm kind of hoping there'll be residual effects of people now, you know, want to work a couple of days from home or some chunk of people will stay home or there'll be more hiring remote now that people have seen it works.

So, we might not grow as fast as we have during the peak of this when everyone was forced to, I'd be surprised if we do, but I do think there's still a tailwind caused by that initial events that won't go back down to zero. I think it'll stay.

Courtland Allen: 12m 41s

Yeah. I'm the same, same sort of feeling. Then on a personal level, I'm trying to, I guess, reconcile my own feelings about how I feel about the end of the pandemic, where it's like, obviously it's a horrible thing and I want it to end.

It was super isolating to just not be able to see everybody you want to you and go to the events you want to. I miss life music and I miss a lot of these bigger gatherings that are with my friends, but it's pretty nice literally never feeling FOMO. Every day that I stay in I'm not missing anything. There's nothing better that I could be doing. That's pretty cool. I love that feeling. That's going to go away.

So, beyond your company, I've been taking a look at your personal website. You got a lot of cool stuff you're working on. Obviously, you're working on your podcast with Derrick, which you already mentioned. That's been going pretty well. I'm a listener. I occasionally catch up.

You won. Well, I should say, you stole from me a very prestigious award. You were MicroConf’s SaaS Podcast Award’s Best Show of 2020. I won Best Hosts and Best Episode, but you got the crown, you got the actual…I got the constellation prize. It was a pretty brutal campaign. It was like attack marketing, you know, I felt personally attacked with a lot of good compliments.

Ben Orenstein: 13m 52s

I remember our podcast episode title was “Courtland Allen must be stopped.”

Courtland Allen: 13m 57s

Yes. I saw that in the feed, and I did a double take. I thought that someone's pulling an April fools prank on me, but you did it. I mean, you were all over me on Twitter. You pointed out some very salient hypocrisy and the fact that Indie Hackers is all for the indie founder, and yet we're owned by what'd you say, a giant unicorn mega corp, which I try to hide. How did it feel winning the Best Show Award?

Ben Orenstein: 14m 18s

Oh, it was great. I mean, it's so stupid because it's just a made-up award, but I wanted it, and when I saw we were nominated, I was like, all right, I want this award.

It was clear. It was like, all right, Courtland is the heavy hitter on this list. He's the one I got to worry about and so, what better to do than to personally attack him and make unfair allegations on Twitter? That's how I understand you win elections these days. So, that's what I went for.

Courtland Allen: 14m 43s

I'm pretty sure that's how you win, and it worked. Yeah. It was weird for me because I always feel the underdog. I'm like, I'm the, the not the underdog in this story? What even is this? Very strange dog.

Well, they're doing it again this year and I've got some plans because I didn't even sic the Indie Hackers fan base on you.

I said nothing about it on the podcast. I put no ads on the website. I just let it go. Let it happen. I said, we'll see how this naturally plays. But next year the gloves are off.

Ben Orenstein: 15m 12s

Good. All right, let's bring it on. I'm going to buy a lot of Facebook ads or something. I might commit fraud. In a way, you inviting me on your podcast is a huge mistake because now you've exposed my podcast to your listeners. So, I'm going to steal 80% of them at least.

Courtland Allen: 15m 24s

People should go check out your show. Art of product, Ben Orenstein, Derrick Reimer. What do you guys do? You basically just talk about, you do what we're doing right here. You just catch up with each other and explain what's new in your lives.

Ben Orenstein: 15m 36s

Two dudes talking. It’s the two dudes talking to format. So, it's we’re each running startup companies, software companies, trying to make them work. Each week we kind of come on and say, what are you working on? What are you struggling with? That kind of thing.

Courtland Allen: 15m 49s

Well, I love your show, dude. I think it's really cool. Whenever I see someone who's very successful and they're still running their podcast, I'm always curious, what do you get out of it? Why do this podcast? Is it just a weekly ritual at this point? Is it moving the numbers in any way? Are you making money from it or is it just pure fun?

Ben Orenstein: 16m 4s

That's a good question. The closest thing is kind of to fund, honestly. We, in the early days, a lot of our first customers came from the podcast. It was definitely a good seed for the business. These days I don't think that. I'd be surprised if many people found us through that.

I just really like it. I like talking to Derrick. I like trying to summarize my week. I like that I can go back almost any length of time and hear a podcast episode of what I was thinking at the time. I went for some, for kicks to just listen to the first episode where I was like, okay, I think I'm going to quit my job and build this thing.

It was just, it was great to go listen to me and hear me say stupid things and be like, wow, I was so naive about this. Or wow, I was really bent out of shape about this thing that turned out to be nothing. It's just a cool record to have.

Courtland Allen: 16m 46s

It's super nice. It's way easier than doing a YouTube show or something that's super high effort. I think more people should do sort of audio format just for their normal lives.

For example, I did a podcast with my friend Lynne on Indie Hackers and she just loved so much having a record that was a snapshot of us at that time. She's asked me, ever since then, can we just do a podcast, not publish it at all and just have it between us.

I've seen others doing the same thing. The creator of the show “Midnight Gospel,” one of my favorite shows on Netflix, every episode is basically an animated podcast. His last episode is one that he did with his mom before she passed away. It was super emotional and moving and he'll always have that record.

So, I just think people should consider buy a couple of good mics, get people you love and care about. Sit down and record something with them and you can always go back and listen to it and it's worth its weight in gold, I think.

So, the other good thing about having a podcast is that sort of putting yourself out there. I was trolling around on your personal website and you've got something on your website that I I've only seen one or two other people do ever, which is kind of a call to action that says by the way, I'm searching for an awesome life partner. Know any smart, funny, accomplished ladies, or are you one yourself? Get in touch.

You clicked the link, and it literally just goes directly to your email inbox. So, you've created almost a Tinder for yourself where at any point in time, people can get in touch and you can find someone to date. And where are you located by the way? You're in Boston?

Ben Orenstein: 18m 8s

I'm in Boston. Yep.

Courtland Allen: 18m 10s

All right. So, if any lovely ladies want to date a successful, smart, eligible bachelor with a booming deep voice who makes me sound bad on my own podcast? You know where to find him. What was your thinking there? Why did you put a dating ad on your personal website?

Ben Orenstein: 18m 25s

It felt worth a shot. That site gets some traffic and I wanted people to know I actually think being set up is great. I think meeting people through atypical ways is great. Everyone's on the dating apps. Of course, I am too. But finding somebody through a more organic channel or it's just a different, just a unique way seems good to me. It seems worth exploring rather than being Tinder profile number 5 million.

Honestly, it's resulted in some dates. I've been on dates with people. It's great. I had this experience recently where I was on Clubhouse talking to my buddy Adam Wathan, and I mentioned being single and someone DMed afterwards.

It was like, oh, hey, you're single. Do you want to do a Zoom date? I was like, absolutely. I realized, I'm really underutilizing my audience, honestly, to find a partner by not talking about it enough.

I have a to do item, which is write up a public dating profile, link to it from my Twitter bio. I'll talk about it on Twitter. I'm glad we're bringing this up now because this is, honestly, a kind of the top priority in my life. Honestly, Tuple is great and matters and is going well, but, God, I got to do the dating thing and it feels like a missing piece right now. So, if your ex were to get in touch with me, you think that seems good? I second it, please do. And please refer your awesome friends to me.

Courtland Allen: 19m 41s

Yeah. It's hard to be on the bleeding edge of anything involving dating. Let's say you're online dating in 2001. It was just weird back then. People would give you crap for it, they’d have all sorts of questions, but now obviously it's completely normal.

I remember being in college, actually in 2005, I think. Facebook was brand new and I actually met somebody on Facebook. I don't know how I found her. The features for Facebook were different back then, but I somehow met someone who was a twin like I was, who was also born on March 22nd like I was, and then we just kinda talked and corresponded on Facebook for maybe eight or nine months.

Then she eventually moved to Boston for completely different reasons. She showed up on campus and we went on a few dates and it was super cool. People were like, that's so weird. You just met this girl online? How do you trust her? What if she's a serial killer? People had all these weird questions, but today, nobody would blink about something like that because everybody dates online.

It gets me thinking, okay, maybe Ben, you're just five to 10 years ahead of the curve. Maybe in five years from now, it'll be super common for everybody on their Twitter profile to link to a personal dating page they have on their website and you're just way ahead of everybody.

I should probably be considering stuff like this too, because. I'm technically single. I date non-monogamously, which means I have multiple partners, but I don't have what we call a primary partner right now. I would love to meet someone to actually spend my life with. I don't know, I think talking about these things in public probably helps.

I think you're probably onto something where if we have a unique platform, we're way more likely to be able to take advantage of something like this. I never really do it. It feels like kind of a no-go zone on the podcast because it has nothing to do with the show is about. It has nothing to do with what my public persona or my tweets are about, and most of my followers are probably guys anyway, but I think you're right.

I think you're smart. Even if it feels a little bit weird, it's probably just ahead of its time. Looked at through another lens, if you are a founder-type person, you're probably kind of predisposed to sort of flaunt societal conventions.

If you did what society said you should do, you wouldn't start a company, you won't be running Tuple, you would get a job. Cause that's the tracks that you're supposed to be on. Anything else it's risky and unproven and it might fail and crash and burn. Dating non-monogamously is definitely that way. Kind of have to make up your own rules and figure things out and a little bit dangerous and scary, but also very rewarding. Also, using your social profile to sort of meet people. Although, it seems like a total no-brainer, for whatever reason, not that commonly done.

Ben Orenstein: 22m 1s

There's still some shame around it. Even, as I'm thinking, even as we're doing it now, I still feel like 5% where I'm like, is this embarrassing? Should I admit this to the world? Should I say these things?

Courtland Allen: 22m 10s

If you go to a bar, for example, if you’re Ben Orenstein at a bar, there's literally nothing that separates you from every other random person in that bar, besides your height and your good looks nothing else separates you.

Maybe that counts for a lot, but you've done all these other cool things. There are a lot of people on Earth who are aware that you've done these cool things. If you have all these tools in your arsenal, why not bring that to the competition basically, which is kind of what dating is in a way. Why be on Tinder swiping and just be one face of millions when you can be your own unique thing?

Ben Orenstein: 22m 38s

Yeah. It feels like a waste to not do that. And honestly, I appreciate your openness, talking about your situation because you don't know who knows people in Seattle. Maybe I know someone who's amazing who is looking for a primary partner, but dates non-monogamously. I can't tell who in your audience, who in the world might be somebody or know somebody that might be a good match. I want to maximize the possible opportunities to, to make that match because you only need one-ish.

Courtland Allen: 23m 5s

Basically. I was seeing a dentist a little while back and she's got both vaccine shots. She’s super excited. We were just talking about dating. She's obviously non-monogamous as well. She's telling me about how at some point in her past a friend connected to her to another person who was like, oh my God, I met another non-monogamous dentist.

It's just like, what are the chances that I would meet another non-monogamous dentist in Seattle? So, they connected the two of them and they went on a few dates or whatever. But yeah, I mean, if you don't put yourself out there and tell people what you're about, no one's going to help you.

I mean, I could give a whole talk about this, how do you make your own luck. A huge part of it is you just literally tell people constantly what it is you're trying to do and what you're looking for. Then magically serendipity happens. For people who don't, you know, who aren't transparent, who don't share what's going on with them, we don't ask for help or who don't put, build in public, they just tend to be much less lucky because people literally can't help them because they have no idea what's going on with them.

Ben Orenstein: 24m 1s

This is actually a great forcing function. Cause I've been meaning to publish this dating profile page on my website. Now I can make sure to do it before this podcast drops so we can throw a link in the show notes.

Courtland Allen: 24m 12s

The other thing is that I think your priorities tend to shift as a founder. I was asking earlier, how do you feel differently now that Tuple's a success? I know that for me with Indie Hackers, I don't know. I spent most of my twenties working a lot, you know, and I had a lot of really good fun vacations and trips and experiences with friends and whatnot.

To some degree, I definitely sacrificed some of my personal life to chase professional goals. Now I'm 33 and it's like, hey, I should, I should reverse that. Professionally I'm doing really well. I feel super secure. There's a lot I want to accomplish, but I want to figure out a really good living situation where it can be as near as possible to friends and family and cool people.

I want to travel a lot and have lots of new experiences. I want to use the sort of things I've accomplished to just live a better life. I want to meet a really great partner and it's much easier to sort of notice the absence of these things and to focus on them once you've gotten to a point where your company is doing really well, at least in my experience.

Ben Orenstein: 25m 4s

Super true. Yeah. I mean, it, honestly, it feels a little bit like a waste where it's like, I can I have all this flexibility. I can go take an amazing trip by myself, or I can leave work at noon on a Wednesday and go home by myself.

It's not nearly as cool to have these things without someone awesome to do them with. I do stuff with friends a lot and, you know, have friends I'm very close to, and that helps, helps quite a bit, but it's definitely not the same. Like you, my focus is definitely shifting.

Courtland Allen: 25m 35s

So you mentioned being on a Clubhouse call with Adam Wathan and this sort of came up, but I was scrolling through your tweets and you've been on a few different Clubhouse calls recently. For example, you had one that was called “Money and Emptiness.” Justin Jackson tweeted that he's going to do this room with you.

I wasn't there. I have no idea what you talked about, like that's the most clickbaity title I've ever heard. I was instantly like, what are they, what's the topic of this conversation? What'd you talk about? Now that I've got you here, I can just ask, what's the most memorable part of that conversation? What was going on?

Ben Orenstein: 26m 3s

It really is just that it's not going to make you happy reality for me. Again, it's so cliche and everyone hates, and it's even cliche to say that saying, this is cliche. This is just infinitely nested cliche. There's no way out of it but here we are, which is like, yeah, I'm making more money than before.

It's really cool. I'm now, as soon as I hit a new level, I'm instantly used to it. It feels normal. And the idea of going down at all sucks. If the dividend is lower next month, next quarter, I'm like, aw, man, we didn't hit the same level as last time. It's like, man, it's just, there's just, no, there's very, I mean, there's very little happiness to be had there.

There's some fun. There's some financial comfort. There's sleeping better at night, definitely. But my brain’s, I think, just not so wired to be like, ah, yes, that is enough resource. I've now reached contentment and happiness and we're good here. Totally diminishing returns. Justin had a different feeling of that.

He was like, no, no, my stress levels have gone down a ton since going from X to Y. And I was like, well, Justin got married at like 19 and had five kids starting at 20 or something. He started having kids really young and has I think five of them.

His finances and my finances are very different. I've been single for a long time. I have no dependents. I was a programmer before this. I've always, yeah, I’ve felt pretty comfortable for a long time.

Courtland Allen: 27m 24s

In a way it's the contrast. He needed to have to be in sort of a bad place where every business has to work because he's been very entrepreneurial despite having a bunch of kids and stuff.

To go from this huge, I don't want to say negative, but very far away from where he is today, Transistor, I think is also making millions of dollars a year to where he is now. That's a crazy change. Whereas to go from a successful, single software engineer who doesn't want for money, you could eat anything you want and you can live pretty much anywhere you want to now having this very successful business, which is great.

It's an accomplishment, but it's not a million miles removed from where you were. It's not gonna, it's not going to permanently change your life and leave you in this permanent state of awe.

I think it's a cliche because the fact of the matter is when you're not there, it still feels like bullshit. If you'd asked me five years ago how would I respond to that person who said, they'd say, oh, it's easy for you to say, cause you're there. Right. But once you are there, then it's like, okay, I get it. This is not, there's other things in life.

Then the after dating, let's say you have the perfect partner that's going well, there's still other categories in life that matter to you. Some would say mental health or spirituality, there's also your own solo sort of hobby endeavors.

I tweeted this thing, maybe the last time you're on the podcast. It's around when I was taking chess lessons before chess got super huge because of that Netflix show, I was just like, you know what? I want to learn how to play chess because my friend keeps beating me. So, I want to beat him.

I started taking chess coaching lessons, and it's a very mundane tweet about how I was paying a guy 30 bucks an hour to teach me chess and it blew up. It’s my most popular tweet of all time, it's got like 2,000 likes. I remember you responded to it. You're like, I love one-on-one coaching. It's my favorite thing.

But you didn't say what it was that you pay for one-on-one coaching for. I didn't know for the longest time until I started listening to your show. It seems like you've got a few things and, I'm curious about what those are and why you pay for coaching.

Ben Orenstein: 29m 13s

Yeah, improving at things rapidly causes more dopamine in my brain than almost anything. It's basically my favorite thing. I love mastering a new skill or rapidly improving it, a new skill. I don't have to master it. It's just going from where I am to better.

Usually, one-on-one coaching is kind of the fastest way to progress at a thing. So, I love being coached on a thing that someone pointing out no, that's not an efficient way to do that. You should do this instead. I've had one-on-one coaching for a lot of things. I try to get it for almost everything that I get into.

The latest example of that probably is maybe illustrative of how much I like coaching is I've been playing this game called Overwatch. It's a video game and we play once a week and I take video recordings of our games. Then I pay a coach to record a video, critiquing our play and telling us how to do it better next time

I want coaching for everything. I want coaching for video games. I get voiceless. I used to get voice lessons, squash lessons, just whatever I’m into at the time, whatever hobby is occupying me, I want to get better at it as quickly as possible.

Courtland Allen: 30m 22s

Super smart. I love that feeling of getting better at stuff. So, for me, for a little while it was chess. Then I was like, okay, I'm pretty good at chess. This is fine. I don't want to be a master or anything. It'll take years and years and years.

Other things are, like this podcast. I don't have a podcast coach, but I hired a podcast boss, who I’ve talked about on the show before, who's just going to sit down with me. She watches me come up with topics and questions and book guests. She just keeps me honest. It's kind of cool. It's almost a little person on my shoulder who's telling me the right thing to do, even as I'm doing the wrong thing and trying to convince myself that it's right.

I guess there's an argument to be made for that anything in life that you actually care about, where you have the funds to get a coach, why not get a coach? I want to get better at cooking. Why don't I have a cooking coach I'm going to get better at my athletic training and nutrition, why not hire a nutritionist and a personal trainer, if I can afford it.

In a way it's kind of like I can't explain why I haven't. Maybe it's fear. Maybe it's just pure laziness, but it would make perfect sense to do it. Maybe I'm afraid that if I have a person who keeps me honest, I'm going to have to do the work that I'm a little bit scared of doing.

Ben Orenstein: 31m 23s

Yeah. I mean, the thing I learned about coaching is it's often more affordable than you might guess. It doesn't have to be every week. It doesn't have to be all the time. You can get occasional sessions, but it's just, so I find it so delightful to have my eyes opened to a thing that was kind of invisible to me before.

When I was working with a squash coach, he would record me playing. He'd be like, you see what you're doing right here? The way you're taking this step, instead of that step, notice how now you're all messed up and you don't have enough room to swing? It's like, ah, the experience of going through the learning process of now seeing a thing that I couldn't see before and then still making the mistake, but at least seeing the mistake and then you start to anticipate the mistake and then you don't do the thing anymore. Now you're just at a new level and now you're looking for new mistakes. I feel so good. I just love that feeling.

Courtland Allen: 32m 8s

Yeah. You've got coaches and they can basically spot everything that you're doing wrong way easier than you and for them it's super easy. For you, it's a struggle.

You're right, it's also kind of affordable. I was looking into, I was talking to Li Jin about this a few episodes back about getting a personal chef, which is not a coach, just someone to literally cook for you. But it's actually, you would think this is the most luxurious thing in the world, you've got to be basically Scrooge McDuck to afford this.

No, it's kind of the same cost as a personal trainer plus the cost of ingredients. You can get someone to come over and cook you a bunch of meals. I've been thinking about startup ideas around this, where there could just be so much more, I don't know, education and teaching, there's just so many people in the world who are good at things and who probably don't like their jobs, but they would be very enthused to teach people about the things that they're good at.

They're really good at crocheting, or they're really good at, I dunno, taking care of plants. I just bought a whole bunch of plants for my place. I don't know what I'm doing. I went to the nursery. I asked him what's easy to grow. They gave me some recommendations. I've half killed some of them already, even though these are among the easiest plans. I would pay someone who loves plants to come over once a month and give me recommendations, like, go do this, do that, buy some more plants, get these, or just go plant shopping with me.

That could be a profession, and they're not going to be super rich. They’re not gonna make a a hundred bucks an hour, but I don't need them so often that I need to, that I would shy away from paying kind of a high rate. Maybe I only need them an hour a month, you know?

I wonder if there's room to build more and more platforms where you can essentially find people who have all these niche interests who are really good at things and just let them make a living as coaches doing the thing that they love enough to be good at in the first place.

Ben Orenstein: 33m 43s

I think I've already seen sort of niche versions of that general idea. Maybe the general thing of we are the repository of all coaches is a hard nut to crack, but I mean, there's sort of the seeds where it's like, okay, like I found my Overwatch coach on a site that matches people with video game coaches. That particular slice is apparently enough to sustain some sort of business.

Courtland Allen: 34m 6s

I found my chess coach on a chess website where you go to play chess, but that also had just a listing for coaches. I should probably do this on Indie Hackers. You want a business coach? There are a lot of people who love their SaaS applications and who love talking to people about it, especially people who are serious.

There should just be a directory on Indie Hackers, hire this person for however many dollars a month or whatever. They'll talk to you about your business and give you one-on-one feedback.

Ben Orenstein: 34m 26s

That's interesting. I mean, I've honestly considered offering that kind of service to people cause I love, it's fun to talk about SaaS and offer people advice and do things. It's the easiest part is the advice, but there's just enough activation energy where I'm like, I don't really want to advertise it and figure it out and all that. I don't know, I would consider it if you had an easy thing to plug into.

Courtland Allen: 34m 46s

Yeah. It’s all the meta work. If you could just basically click a button and there's a call and you know who it's going to be, and you've got a little briefing of what they need, and you can just talk to them. You don't have to do any of the work sourcing, people were getting paid or whatever, then suddenly it's worth doing.

Who wouldn't listen to you talk, right? You've grown your business to millions in revenue super quickly. Pretty much 99% of founders never get to that point. It would be rewarding for you probably. Maybe the downside is that you'd be spending even more time on startup stuff and less time dating.

Ben Orenstein: 35m 13s

That's a good point. Also, in the classic mom test fashion, you definitely can't trust me when I say that I would totally use that.

Courtland Allen: 35m 21s

Yeah. I'm going to go out and then just build this whole thing.

Ben Orenstein: 35m 22s

Yeah, in actuality, I kind of am busy, sorry.

Courtland Allen: 35m 25s

Sorry, dude, I'm not gonna use this. I don't know. I think it's an interesting idea enough to explore it.

I think looking at where you've come, it’s cool to do this catch-up episode. So, hopefully I can get you back on. We can catch up at least a couple of times a year, just to see where you're at, but I'm pretty blown away by how far you've come.

We talked about COVID driving a lot of the growth and a lot of traffic, but people are going to be pissed off at me if I don't at least ask you some questions about how did this happen? What did you guys do at Tuple to sort of drive this growth? What besides COVID what, besides like this huge shift to remote work has gone really well for you in the past year?

Ben Orenstein: 36m 1s

One thing that we did that I think was good was we hired a salesperson. I'm a programmer by training. was getting these sales leads from people wanting to purchase annual plans or things or buy Tuple from larger companies.

I have a hard time being patient with those people. It's an extremely inefficient process for large companies to buy, most large companies to buy things. I would like try to be like, how do we do this really efficiently? I would try to change their process or be kind of ornery and refuse to give them things they would ask for. I'd be like, that's just, what are you talking about? That's not the best way to treat your leads probably.

We hired a salesperson who's just doesn't mind this stuff. He doesn’t mind that he has to sign up for a stupid website and then punch in the invoice manually rather than just send them the Stripe invoice and have them pay with the credit card. H doesn't love it, but he doesn't mind it. I hate it.

It took something that like, I hated that the business kind of should have someone doing and like had someone do it, who doesn't mind it. And I was like, ah, that was, yeah, there we go. Delegation that's that seems to be what this is for.

Courtland Allen: 37m 5s

I think it's pretty magical when you can learn that when you learn that you can hire someone who is not only better certain things that you didn't think anyone would be better than, but then they actually liked some of the stuff that you didn't like.

Our community manager for Indie Hackers, she actually just left. She was here for two years. She turned into a celebrity and just graduated and was like peace guys, which is kind of cool to see, but she's just super good at running community. She does a lot of the personally tedious things on the forum that just I hated doing and she loved doing it. I

t was her favorite thing, wake up in the morning and do. That's just mind blowing to unlock that when you've spent years probably grinding away in your startup, doing everything by yourself.

Ben Orenstein: 37m 41s

I knew sort of intellectually that there was a reason companies hired people. When it came to it, I was kind of emotionally like no one's going to do this thing as well as I can. Will we ever be able to find a good person that does X? No one likes to do sales. It's so annoying. I was like, no, you dumb dumb.

That's been kind of a good thing for me over this course of the year, which is as we started hiring people, I'm starting to see and appreciate it a more visceral level, the power of delegation. Just the fact that it's a win-win-win where I don't have to do this thing anymore. This thing is getting done and it's getting done by someone that likes it and is good at it.

Courtland Allen: 38m 19s

So what's the future look like? Is there a point where you hire yourself out of Tuple and you can kinda just sort of watch the machine run by itself? Or is that not something you'd want to do?

Ben Orenstein: 38m 30s

I don’t know. It's not clear. I have a hard time projecting that, into the future that much and knowing what it's going to feel like. I could see doing that. I have friends who've run businesses where they eventually hire management teams to run them and they just advise basically. That seems pretty cool.

If I got time, it's probably gonna come down to kind of novelty and interest where it's as long as my day-to-day changes and I have new things to learn and new stuff to get coached on and improve at then I'm probably good for a while. A company so far seems to be a very good vehicle for that because it keeps changing.

The thing you need to do each month to be successful is different. The challenges are different and it's different every time we hire a new person. But I think at some point I could see myself being like, you know what, I'm tired of thinking about pair programming and I'm really excited about this other idea over here. At that point I might, you know, there's a few options of how you step back and what it looks like. It would probably happen at some point.

Courtland Allen: 39m 30s

I think about that all the time, too. It's so hard to figure out what would the next thing be? Because there's a bunch of different options. Do you just pick something, like Pieter Levels, for example, he's just a craftsmen who just likes working on things that he can perfect and that he's curious about.

He's not trying to one up his former self, he's just like, this is really cool. I want to experiment with this new technology or this new trend, et cetera. That's what motivates him and he's super locked into that.

Whereas another approach is to just one up your previous self. You know, I built a company to millions in revenue, let me start a VC-funded unicorn company and see if I can just go big. As cliche as that is to do, there's a lot of validity to that why not set your sights higher? Once you get to a certain level, you know, like once you graduate high school, you want to go to college.

Then there's another approach, which is just completely leave the domain altogether. You've had your life as a tech founder and software engineer. Now you're going to have your life as a singer songwriter or as a novelist or something. It's hard to pick which one you want, you know, but it's also cool to be in a position where you could probably live multiple lives, multiple careers, because you're able to sort of find success in one at a young age.

Ben Orenstein: 40m 39s

That's such a lucky thing to have. I don't really worry about finding the next thing because I eventually get into something. I just love new stuff. I think the thing with Tuple was like, I wasn't like, okay, I got to start a company, what are we going to do?

It was like, the idea for Tuple was there and it was like, I think I have to do this. I don't think I would be like, okay, I want to leave Tuple and go do another thing, let me just kind of figure it out. I think I'm just going to get distracted by a thing and be like, oh man, I'm kind of obsessed with this. I feel like I kind of have to do this thing and then I'll have to figure out what to do at that point.

Courtland Allen: 41m 12s

What's your advice for founders who aren't in your position yet, but who might someday be in your position who are maybe on the verge of achieving the success that they've been dreaming of, what do you think they should take away from kind of what you've learned in the past year and a half running Tuple and seeing it grow to such a large size?

Ben Orenstein: 41m 28s

It'd be great if there were just kind of one or two things that I knew that were a secret that I could just whisper it to people and then it would work for them, too. But I don't know.

I think we did a lot of small things right. Make sure to do a hundred things right is not helpful advice. Our path is so hard for me to tease apart what were the things that were key choices, what was kind of luck, what did we succeed despite of, it's like, it would be, I think kind of unfair for me, or just not really genuine for me to be like, ah, here you go, here's your one or two quips that will send you on your way.

Courtland Allen: 42m 3s

But in a way that is like a single quip, which is there was no single thing. If you're a founder and you're doing a hundred little things, you can't escape from the question, if you're a founder doing a hundred little things…

Ben Orenstein: 42m 14s

We'll reduce you to a small anecdote.

Courtland Allen: 42m 17s

A one quip so we can take out of context, that everyone can disagree with you on Twitter.

Well, folks, you've heard it here first on the next podcast, a bunch of potential useless advice, but maybe good advice. We don't, we're not really quite sure. Ben, thanks for coming on and shooting the sit with me and doing sort of a funky catch-up episode. Hopefully you'll come on again.

Ben Orenstein: 42m 35s

Dude, I'd love to, it's always fun. It's quite a pleasure and good luck this year at trying to win some awards.

Courtland Allen: 42m 42s

I'll see you in the SaaS Podcast Awards 2021. Gloves are off this time.

Ben Orenstein: 42m 45s

Sounds good. Bring it.