The single stickiest thing software can do is collect money from a customer, because once payment flows are embedded, customers find it extremely hard to stop paying or to figure out an alternative.
Steven Sinofsky argues that beyond features or workflows, the deepest source of software stickiness is simply being the system that collects a customer's money, which creates powerful organizational inertia. ✦ AI generated
Steven Sinofsky · a16z Podcast · 2026-07-07 · original ↗
starts at this moment · 11:56
“Historically, what has made software sticky and how are agents starting to disrupt that?”
The most sticky thing you could do is actually collect money from a customer. And if you're collecting money, it turns out it's really really hard for them to stop sending you money. And it's really hard for them to figure out what to do if they stop sending you money.
verbatim transcript · starts at 11:56
11:56right. I I think it's important to also consider that the most sticky thing you could do is actually collect money from a customer. And if you're collecting money, it turns out it's really really hard for them to stop sending you money. And it's really hard for them to figure out what to do if they stop sending you money. And and it it sounds really trit, but the the stickiest software is
12:19software that's getting used somewhere. Then when you dig in and try to come up with reasons, well, it just depends on who you talk to in a company, you know, you talk to the HIPPA compliance people in some company and they're going to tell you this is the software you have to use because it's like the most bestest HIPPA compliant software. If you talk to the administrators, you're going
12:40to hear about onboarding new users. If you talk to the users, you're going to hear about muscle memory and keystrokes or labor unions or whatever. and and so you have to be yet you you really want to get the software sold and that's your fastest path to sticky and after that it it's sort of you know a winner's tail over over what caused it to be sticky
13:05and and in fact the best thing about sticky is if you're the rep for a company that you've sold something to and the company is threatening you like hey we're going to replace you we're just going to listen to them and you're going to find what's sticky. And if that works like three or four times across different accounts, then you've just told the tale as to what made the
13:27product sticky. It doesn't matter what the PMs or what anybody else thought of. It could be some crazy arcane thing, you know, like I have stories of lots of sticky software and lots of arcane things, but like anyone who's ever tried to displace um Microsoft Outlook as email very quickly learned about delegate access and and having calendars owned by multiple people and all of this crazy stuff. And like I can tell you
13:55there was no meeting where we said, "Okay, let's figure out how to make the calendar the sticky part of Outlook and make sure we handle recurring meeting exception handling well." And then you go and you find out, you know, General Motors isn't going to displace like 600,000 seats because of the calendar or some crazy thing like that. And so you can, it's really amazing in enterprise software what causes sticky and how you