Gusto

“We didn't follow on. We didn't raise our hand to be the big dog in successive rounds. And it had nothing to do with the quality of the company. And people trust us when we explain that because the company was a wonderfully engineered, great SAS company deliver…”

“It's my biggest, single biggest angel investment ever, and when I met Josh, it took me like 15 minutes to commit, and I didn't see even one page of the product he's building”

“So for example, a few years ago, I invested in a set of companies based solely on the fact that I would have used them at my first startup. I would have used Stripe for payments. I invested in Stripe. I would have used Mailgun for email, and so I invested in M…”

“In the very first board meeting, Josh said, we have this competitor called Zenefis, who I had met. I knew what the company was doing. They're going exceptionally fast. They've got a business model that's working really well, and they're outpacing us significan…”

“So we knew at the time that ADP and paychecks were We're pretty crappy software companies. Like the software was terrible. There was not a monopoly on either side. Both companies, you know, had roughly equal market share.”

“This idea of kind of like firing yourself from your old role and hiring yourself to the new role is something that I think the three of us really took to heart and it's been really helpful.”

“It's the highest open rate email probably ever.”

“You can't add delight later. When you look at a product, our experience, you have to think about delight as an inherent part of the product itself.”

“So the way to solve it is not for us, it is not like cut the delight element out. It's got the functionality down. It's scope it down to a place where it's small enough that you can test it and then ship it.”

“So I think 80% of this is really solved by hiring. And the other 20% is solved by making sure we don't miss out on opportunities that are not directly staring us at the face.”

“In the early days, Josh and I, we're meeting together every Sunday for four hours, five hours in, in Eddie's apartment building in San Francisco. And we were just talking about these, exactly these types of things, how to handle these things.”

“Instead of getting to the next revenue milestone, in five years, we're going to get to shrink it to three years.”

“NPS is not the one metric. Like, it's not the one place you go and you know everything about how people think about your product or love your product at all.”

“We're serving over a 100,000 small businesses across the country, across all these different industries.”

“And for me, the way I think about this is a brand or a product experience is really like some, like a product is like a personality. It's like a person. And when you meet someone for the first time, the first 20 seconds, the 1:30 seconds really, really matter.…”

“The other thing is about comments, and you know, we have like a Slack channel in Gusto, it's open to everyone, where literally every single NPS comment has been read by many, many people in our Gusto team, and especially The product and design teams.”

“We're still doing this today, which is thinking about investors as team members. When you bring in a new Gusti, that's how we call our own team members. When you bring in a new Gusti on board, there's an interview process, right? And there's like a whole lot o…”

“So I think the company eight years ago when we started, we were three and now we're around 1200 people.”

“And, you know, I was able to write the first check in the, you know, companies like Robinhood or Platt or Gusto or Flexport.”

“Maybe it's not even until after five or ten million where if you don't have capital, you can't all be Atlassian or Qualtrics. Or, and they fall behind competitively. And I think that's the trap of the fallacy of the lifestyle-esque business, right? Where media…”

“I believe the best opportunities find you at the end of the day. It's not that you don't find them. Okay. But they also find you by the same token. And if you're gonna pass on an amazing binary set of founders, an amazing CEO, CTO, just because they're in a co…”

“We changed our like salaries and gusto to 500 dollars a month.”

“They are not always expensive, but they are often expensive. So if I look back at our portfolio, Gusto was expensive. Zoom was expensive. Yammer was expensive. A lot of the good ones, Ironclad was expensive. But some of them weren't. Viva wasn't expensive beca…”

“We had just invested in Gusto, which was a competitor that was growing not quite as quickly as Zenefits. But the reality is Gusto has endured and become a massive company, and Zenefits didn't.”

“I think I underestimated both the founder and the openness of the market to switch and I'll say something else, the willingness of investors to pay up quickly for that, such that it got outside my price range very quickly, right? Stuff happens, you know, and y…”

“Yeah, that fund is one of our Two or three best funds, and just to tell you what was in it was Livongo was in that, Snap was in that, Circle was in that, Gusto I think I'm missing a few others. It's probably gonna end up being a, you know, 13 to 15 X fund.”

“The normal has changed. We used to think about, hey, you go, like when we did Samsara and you know, Gusto and some of these companies are like, yeah, triple, triple, there you go, triple, triple, triple, double, double, right? And you look at these companies a…”

“I lost a Series A of Stripe. I lost a Series A of Samsara. I lost a Series A of Snap. And the first one I won was a Series A of Gusto.”

“It might not have hurt to sell Gusto. I think Gusto's a great business, but I think, you know, they were valued at ten billion at one point, and I think they're still gonna be a strong business. I don't know if they're gonna have explosive growth from there.”