What's up everybody? This is Cortland from NDHackers.com and you're listening to the

NDHackers podcast. On this show, I talked to the founders of profitable internet businesses,

and I try to get a sense of what it's like to be in their shoes. How did they get to where they are

today? How do they make decisions, both at their companies and in their personal lives? And what exactly makes their businesses tick? And the goal here, as always, so that the rest of us can learn from their examples and go on to build our own successful companies. Today, I'm talking to Ben Orinstein. Ben is the co-host of The Art of Product, a podcast about the intersection of code and business, but is also the CEO of a new company called Tupil, which he and his co-founders have been bootstrapping for just over a year now. They are in the very early stages, but they're on the path toward profitability, and it looks like they're going to get there. So things seem to be going really well so far. Ben, welcome to the show. I'm excited to talk to you about this journey you're on and how you guys are navigating the treacherous waters of being an early stage startup. 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. Well, I like having founders like you on the podcast, Ben, because you're 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, Tupil could be a wild success. A year from now, Tupil could be dead and you've moved on to something else. We don't know. You're in the middle of it. Yeah. It's real life drama. It's reality television happening now. that's exactly it. And I can tell you I've been surveying different segments of the

Indiacers 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 experience has been because the things you've been grappling with for the last year or 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? 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. And so I tend to stay involved in like a hobby or something as long as I'm making rapid progress and getting better quickly. And then once I've like kind of like gotten my feet underneath me and I can kind of see like, okay, now it's just a bit of a slog to get to like actually grade at this. I usually lose interest. Hopefully that won't happen here. I'm hoping that starting a company is like dynamic

enough that there's enough new things I can jump into that it doesn't become boring. My hunch is that's

the case. Yeah, I was actually planning to ask you what would have to happen for you to regret this

decision of becoming a founder. And 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. 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. Like, I had a great job and it was an interesting job. And my, like, 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 turn south tomorrow and we, like, just went down to zero, I wouldn't look back on this and be like, oh, I shouldn't have given that a shot. I would, it'd be okay. 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 going to be fine. Then it really makes it easier just to appreciate running your startup in the moment. 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 like 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 like 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 like regretting not doing it. 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've been turning over in the back of your mind for years? How did that go? 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 like applying my skills to a thing that I was

fascinated by. And so it seemed like I was going to do this eventually. And so 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 I just, over a couple months, I just got the itch. I just got dissatisfied. And I was like, you know what? I think now's the time. Like, 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. And so it was really over just a handful of weeks where I decided to pull the trigger. 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.

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