The Wisdom Wall

19 quotable lessons, heuristics and mental models. Every one is playable at the moment it was said. No fortune cookies allowed.

Everyone Jason Lemkin (550)Dave Kellogg (85)Sam Blond (68)Christoph Janz (51)Michael Seibel (38)Mark Roberge (38)Nick Mehta (36)Kyle Norton (28)Vidya Peters (26)Brendon Cassidy (25)Amelia Ibarra (24)Brian Halligan (20)Henry Schuck (19)Aaron Levie (19) Best Newest Oldest

“I'm actually very bullish right now. You know, there's like a little bit of a meme of like these AI coding tools. You can just swap them out. I think that's like a temporary thing that you'll see on Twitter or X or whatever. I think the mode is actually fantastic because if you're the place where you have agents that…”

Aaron Levie, Jul 2, 2025

“You do want it to be kind of just healthy to be at a six or eight X revenue multiple, and I make, I'm making up those numbers, but like, but that, you know, that tends to be a safe range if you assume the company's going to get 20, 30, 40% operating margin, grow it up, you know, 10 to 20% revenue rate, like that, that…”

Aaron Levie, Dec 6, 2023

“The alternative model is you just say, hey, we're just going to embed AI into everything. And then you're like, well, shoot, now my costs just explode. And, and, and also equally, you have this, like, you know, disadvantage, which is the power user is being subsidized by the non-power user, which, you know, has in, in,…”

Aaron Levie, Dec 6, 2023

“There's no AI budget per se. When I, when I, and when I referenced that, it's sort of like, there's every, everybody has like just some discretionary dollars for, you know, some R and D or innovation thing. And so that's, that's probably right now the totality of the kind of quote unquote AI budget. And you should be…”

Aaron Levie, Dec 6, 2023

“Once you understand that dynamic, then actually the, your growth and your scale of your business is actually most functional to how much you invest in, in scaling it up. So once we figured that part out, and once capital was relatively cheap, we just decided, well, why don't we just go and scale as fast as possible,…”

Aaron Levie, Feb 26, 2015

“in the nineties and you had to sort of top down sell your software to get in, in the first place, then you had to make some really, really key early trade offs. Like you had to actually decide where am I going to get a flywheel effect going? And you don't really get a flywheel... there's no such thing as the Fortune…”

Aaron Levie, Feb 26, 2015

“Think about AI is actually a change to the labor model of using the software. So what, what can you do in a world where you can effectively create digital workers that That can go automate anything, you know, within the confines of, of your software.”

Aaron Levie, Jul 2, 2025

“So, so we can now effectively think about our software as having labor attached to it, which for all of us building enterprise software is like a completely mind bending, you know, concept where we're no longer just limited by the number of people that we sell to in an organization. So if I'm building legal software, I…”

Aaron Levie, Jul 2, 2025

“What is the new network effect in a world of AI? And it's some degree of, of that user working with an agent to create something by creating something that data feeds back into the agent's futures capabilities. And you get this sort of flywheel that, that ends up being pretty positive”

Aaron Levie, Jul 2, 2025

“I think we look. Like probably what most companies are gonna have to look like at some point, which is you're probably growing teens. You're probably generating 30 plus percent operating margin. This is sort of the historical norm for software companies, and you should get as many years of 50 to a hundred percent…”

Aaron Levie, Dec 6, 2023

“because end users don't want to buy platforms. They want to buy features. And so we, we got in through the feature and then we were able to ultimately turn that into a platform.”

Aaron Levie, Nov 12, 2021

“a lot of companies confuse getting to know your customer and, and that customer intimacy with, with building whatever they ask for. And that's obviously the road to, um, to, to, you know, uh, essentially all of the, the broken enterprise dreams that we've, we've always had”

Aaron Levie, Feb 26, 2015

“The amount of work you would have to do to pack into, let's say, a non-reasoning model for giving it exactly the right sort of context, instructions, kind of hacking and tool use, versus today, just having O-Tree go do that, or having the new Lama IV go and do that with reasoning capabilities, you instantly have now…”

Aaron Levie, Jul 2, 2025

“The things that transcend AI will become probably then even more important because they, they will be the things that separate the sort of flash in the pan, you know, overnight success that then fizzles because the founding team wasn't really in it for the right reasons, or they weren't really thinking through how do…”

Aaron Levie, Jul 2, 2025

“at the sort of final, you know, kind of the terminal point of, of your business, it's, It's to produce a certain amount of cash that goes back to investors. Like, if you just, like, why would you give a dollar to something? It's because you want cash back at some point. Like, beyond, and, and the equity appreciation is…”

Aaron Levie, Dec 6, 2023

“Is architecture matters more than almost anything else you can imagine, uh, in that journey. Because if your feature is then completely disconnected to the next feature, and then thus the next feature, then you really aren't on your way to building a platform.”

Aaron Levie, Nov 12, 2021

“you align your time with where the, the, ultimately the dollars are gonna come from, and so, in the base, we often will have lots of customers that have significant expansion opportunity, and that can look as important or, or be as important as a net new, you know, logo that we have to go get.”

Aaron Levie, Nov 12, 2021

“the more you can be taking existing spend, existing categories, but just changing the variables a bit, so they, they favor your strategy. So what we do is we go to customers and we say, what if you had one solution that did all of these things, as opposed to buying individual products that do parts of those things?…”

Aaron Levie, Nov 12, 2021

“if you're building a deep industry workflow, you actually could make more money from that customer than we can.”

Aaron Levie, Feb 26, 2015
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