Sam Schillace

When we did Writely at the beginning, we didn't even ask for an email address, because it was such a novel thing. We didn't want any friction at all in the onboarding process. So you could just come in and make a document and start using it without telling us anything at all about yourself. And after about two minutes of typing, if you're still there, we'd very gently just say, 'Please give us your email address, no password, no anything.'

If you're very pessimistic, you might miss the surprising result that pops out of an experiment. You might force yourself to do a bunch of experiments grudgingly, but you're like, 'You know what? I hate this. I'm doing four experiments today because I have to do it because I want to be an entrepreneur, but it sucks and everything's miserable and black.' And then you won't notice that, oh, this thing didn't work, but it didn't work in an interesting way.

Every new idea looks dumb at first. Unfortunately, the dumb ideas also look dumb at first. It's not a perfect [filter]. But the more disruptive they are, the more dumb you're going to feel they are. You always listen for stuff like if they say it's a toy or if it's practical or it's stupid or I don't get it or whatever, those are often... Toy is a good keyword. If you hear people saying something's a toy, that's often a really good signifier that it's actually something real and threatening.

And that bifurcation of love it, hate it, is really how you have an idea of whether you have impact in what you're building. If you get more of the bell curve of modern indifference and maybe mild like and mild dislike, that's an incremental product. That's not really disrupting anything. But if you look at something like ChatGPT where the entire world is like, 'This is amazing.' Or, 'This is terrible.' And there's not a whole lot in between, that's a very good signifier of it being truly impactful and disruptive.

People are lazy. Look beyond cool too, on how much easier new tool or tech makes someone's life. Convenience always wins.

Users will only adopt what you're doing if that sum total of energy that they have to expend is less than the resulting ease in their life that they get, usually by a factor of at least a couple, right? So it has to make your life a lot better, hopefully a really a lot better, like 10X better than what you spend to use it.

It's all about user value. Users are lazy, right? We're all lazy. We don't really care that much at the end of the day. No one's going to do something really in their life for any other reason other than it makes their life better. Nobody cares that you're friendly or nice or the logo is pretty or whatever. They care about making their life easier.

I think there's this really deep thing that people have where if something is disruptive of your worldview, it feels threatening, and you have this very stark choice to make that's either you're wrong or it's wrong. And humans are storytellers. It's very easy for us to tell stories about why something is right or wrong if we're motivated to.

Every new idea looks dumb at first. Unfortunately, the dumb ideas also look dumb at first. It's not a perfect [filter]. But the more disruptive they are, the more dumb you're going to feel they are. You always listen for stuff like if they say it's a toy or if it's practical or it's stupid or I don't get it or whatever, those are often... Toy is a good keyword. If you hear people saying something's a toy, that's often a really good signifier that it's actually something real and threatening.

And that bifurcation of love it, hate it, is really how you have an idea of whether you have impact in what you're building. If you get more of the bell curve of modern indifference and maybe mild like and mild dislike, that's an incremental product. That's not really disrupting anything. But if you look at something like ChatGPT where the entire world is like, 'This is amazing.' Or, 'This is terrible.' And there's not a whole lot in between, that's a very good signifier of it being truly impactful and disruptive.

I think products almost follow these thermodynamic rules where if you add a little bit of value, your adoption goes slowly and if you add a lot of value, your adoption goes really quickly, right? I think ChatGPT is a great recent example of something that was just added a ton of new value to the world and got this explosive growth.

You're always wrong about products. That's one of my other rules is you're just always wrong. And so you have to try it. You have to put it in front of people. You have to try it yourself before you'll understand it. No one can really design products in their head completely as far as I can tell.

We tend to undervalue the things we're good at. We tend to think work has to be unpleasant. And so if something is easy and fun, we don't tend to think it's valuable. So I think lots of people gravitate in this direction of like, let's go do unpleasant things and grind our way through the career because that's the way to make it. But the reality is you should go do the thing that you feel guilty to get paid for, if there's a thing like that, and do the hell out of it, right? Do it as hard as you can do it.

I think the way you get extraordinary returns is you do extraordinary things, right? You have to take bigger risks, and have more interesting shots to have this kind of extraordinary result in your career.

I think there's, at the end of the day, the reason you get ahead in your career is you had a lot of impact. And the reason you had a lot of impact was because you picked something that you're good at that you did with a lot of intensity that wound up having impact, right?

Work doesn't necessarily have to be hard. It often is, but it doesn't have to be. And the best case is that it isn't. The most impact you'll ever have is where you're in that mode where you're just in the flow and doing your thing and you're happy to do it and you can't quite believe they pay you and you don't understand how you're getting away with this, but it's super cool anyways, right?

We made this choice with... So it's a little hard to remember, right? Because it's like 18 years, 17 years ago now, 18 years ago almost. In that era, Office was impregnable, right? So software had to be distributed physically, right, it had to be shipped around, it had to be bought and installed. It was harder to use. And so there's a very high transactional cost. Because there's a very high transactional cost, the buyers would always make this decision like, 'Do I want the thing with 1,000 features or the thing with 995 features? I don't know what those last five are, but I might as well have all of them.'

I think AI isn't a feature of your product. Your product is a feature of AI.

Really transformative massive value will come from building apps and solutions that won't work at all without it, that treat it as a true platform.

I think the way that the internet made distribution of information free, I think AI is going to make pixels free. So pixels are expensive to produce now, they take programmers and they take lots of infrastructure, and putting a pixel in front of the user is a hard thing to do and lots of software is predicated on that.

If we'd gotten it in the other order, we might not have done it. It's another good example of why not and what if, right? Where we got really lucky that we saw the what if part, that we saw how cool a document in a browser that you could collaborate on would be, because if we understood how hard the collaboration piece would've been first without understanding that value, we might've been like, 'Eh, it's not worth it. It's going to be so hard to solve that problem.'

And we made this trade-off, we're like, 'Look, we're easy to use, we're zero install, you don't have to ever deal with it, it's super convenient. Plus you get this one new feature that's really, really useful, which is collaborating with each other and not having to send attachments around the old file servers, but we're going to take away most of the features, because we don't care about them that much.'

I think the way you get extraordinary returns is you do extraordinary things, right? You have to take bigger risks, and have more interesting shots to have this kind of extraordinary result in your career.

We made this choice with... So it's a little hard to remember, right? Because it's like 18 years, 17 years ago now, 18 years ago almost. In that era, Office was impregnable, right? So software had to be distributed physically, right, it had to be shipped around, it had to be bought and installed. It was harder to use. And so there's a very high transactional cost. Because there's a very high transactional cost, the buyers would always make this decision like, 'Do I want the thing with 1,000 features or the thing with 995 features? I don't know what those last five are, but I might as well have all of them.'