Expensify

“We take our whole company overseas for a month every year. We just got back from Uruguay. And so we brought, like, a 130 people to Uruguay.”

“We're a hundred percent inbound it's we don't do any advertising, we do no outbound calling whatsoever and it's all just organic from the bottom up, and it works amazing.”

“It is just a brutal, awful slog in the start, and so as much of this conference is about getting to that hundred million, really, I mean, the hard part is getting to that, that one million. Like, that is the valley of death that basically will wipe out probabl…”

“The greatest companies don't happen because suddenly, miraculously, everyone in the boardroom always agreed on every single decision. That's never happened. The way it happens, great decisions are always controversial.”

“The part of the board, like the purpose is not to actually collectively run the company, but it is to serve a check on your power.”

“If I wouldn't pick one person, I'd pick 50 people, and I'd call them all the time and I wouldn't, and I would consolidate their knowledge, and then I would present that consolidated answer to my actual board, people that have, like, some influence over me.”

“Actually I have no independents on my board, because I don't like wild cards.”

“There's like, build a viable business which you care about things like profit margin, things like this, or you just sell to a bigger sucker. Overwhelmingly, Silicon Valley is based upon the latter of those, and like, the reality is at no point relevant in actu…”

“Again and again, every single big round we have, the employees get fucked. And there's a whole bunch of reasons for that. It's like the VCs always win. The founders sometimes win. The employees rarely win.”

“This whole idea of getting a gigantic war chest, I think that's bullshit. Like, I think that it's just a big waste of money and capital, and it just, like, ruins your company's culture.”

“How many of those same people just brought in some kind of outside executive from their VCs? Yeah, you just fucked your entire company. Because by doing that, you just indicated to every one of your employees, you cannot grow here. That we value skills that yo…”

“I just think it's all bullshit. Like, I think the reason the valuations are high is because there's a shit ton of money in the markets, and it has no place to go. Like, there's, we just printed, what, three and a half trillion dollars of stimulus money out of …”

“This, like, the seed and A are primarily just about, like, you and the story you tell. Like, especially the seed. A, it's like you have to have some evidence that, like, you know, the story has some anecdotal evidence of some kind of traction. And then, like, …”

“When Brex and Ramp and Expensify and Divi, all of them are worth billions, it changed. Not only did it change the size of outcomes, but it changed the way we invested. We didn't have to decide who was number one.”

“A huge percentage of what customers are asking actually is very simple. Or mid-level simple. It's not super complex. So, all of it went to the lower tiers, and what remained went to the higher tier, but since we were already staffed up there for the, for all o…”

“What we learned is, in fact, outbound calling didn't quite work for us from an economical perspective, even if we did it offshore, so we sunset that team, and we learned that onboarding specialists We're very, very encouraging in terms of their ability to conv…”

“And Expensify is a cash positive business. We're very proud of it. We've had growth and profitability for something like five years now.”

“As we grew customers on the platform, there, so the number of active users on the platform grew, which was amazing, because that's how our revenue grew, but for every dollar of revenue that we brought in, we had to spend almost a proportional amount in support…”

“If you're experimenting with ideas, if you're not quite sure about a strategy but you'd like to try it, so long as the role itself lends itself to outsourcing, consider outsourcing before you really commit and hiring a full-time team. Because once you hire a f…”

“What people say they want, what they say is indispensable, and what they tell you about how they'll use a product is just phenomenally different from how they actually end up using the product, and from their willingness to try something versus, you know, prop…”