The Ledger, every show

“Toast. No chance. Because it doesn't have e-money licenses in the UK. Because it doesn't have PEO licensure in, you know, the 18 states in the US or whatever the number is that require it. Because it doesn't have the regulatory arbitrage that we have, because …”

“What I would say about other companies that are doing AI products is that for the longest time, their roadmap sucked. They didn't know what their next proximal feature was going to be that was going to generate revenue. They didn't have another skew idea with …”

“This company, you know, is pretty well known, and they've got a good SMB payroll business going, but like, at a certain scale, they switched to Workday. When they switched to Workday, they stopped using their own product, and when they stopped using their own …”

“Coaching is stupid. Most of it is just vapid blood sucking on the part of people who weren't very good operators and decided to make a career charging people by the hour to tell them how to be good operators. That's like 98% of the market.”

“If you have never taken something from zero to one and you've only ever actually worked in large companies, Then you are at a disadvantage in trying to navigate the early years of your own company. It's just way harder to know what good looks like.”

“When I joined Rippling, we were at something like four and a half million bucks in revenue, which by itself is a very exciting number, I think, going from zero to something. But in hindsight, obviously, it was very, very early in the company's business, in the…”

“You learn way more from success than you do from failure because success teaches you the things that do work as opposed to eliminating one of the 10,000 things on the list that don't work.”

“Every time you find yourself doing meta work, you should have a micro panic attack because you are burning precious time on something that yields no benefit to your business. It's a necessary evil, but it should be minimized. And so you asked about like, you k…”

“And I think in the next five years, a lot of the value of AI is going to be most apparent and captured by the businesses that have the underlying data and tooling to do quote unquote deterministic things or perform tasks in the software world”

“I am skeptical as to the survivor, the survival rate of many of the AI companies that I see starting today because they're going to perpetually drink their data through a straw from other systems. And those other systems are never, ever, ever going to let othe…”

“The PM design and engineering jobs in their most coarse grained forms, not in their like, really find detailed forms, but in their core screen forms as roles are all converging.”

“Most companies, again, set aside the outliers. Most companies that find wild success find it pretty soon, find it pretty early. They find it because they were in a good market. They find it because the founder had an earned secret that they could use to build …”

“Especially as an early stage company, don't do business. Don't take money from, Funds that are in any way loss averse, because that's where they get into this sort of pernicious misalignment of incentives you know, encouraging you to keep going because they do…”

“There's a new product that we're just releasing called talent signal. It's the ability of this system to read the work product of employees and like marry the data that we have. On whom you've hired into your company at what job level with what, you know, all …”

“And so, TalentSignal, by reasoning from the work product only, Like it doesn't have access to demographic data. It doesn't know your race, ethnicity, you know, your age, your work location. It just knows this is the source code you wrote, or these are the cust…”

“We didn't build a chatbot. We didn't build a co-pilot. We didn't build any of these surface level obvious capabilities. We're gonna build them. They'll be in there at some point. Who cares? It's not gonna sell a single extra subscription of software.”

“One area where my CEO Parker spikes is like, he's very direct, does not pull any punches. He almost, you might even say lacks empathy when it comes to delivering a directive or difficult information to somebody.”

“The CEO job, the most successful CEOs act with impunity in the work environment in a way that number one, a good CEO doesn't really think about it. And number two, a good second in command does think about that and enable it.”

“Every successful outcome is led by a founder who is deeply impatient, really impatient.”

“All of our teams at Rippling are pretty deliberately understaffed and people feel it and they'll complain about resourcing, but like at the end of the day, a team of five that ought to be seven is way better than a team of nine or 10 that ought to be seven.”

“The cure to politics is not to lecture people about being apolitical. It's to make sure the team has too much to do.”

“Parker still approves every expense over five dollars personally. He still runs payroll for the whole company globally in our product.”

“I'm friends with many CEOs who I've, you know, met over the years of having been one and then doing this job, and the folks who are really into the coaching and really into the touchy-feely stuff for themselves on the balance just have not performed as well as…”

“If you ask someone for relevant experience, then if they have some first advantage is that like you get to integrate their experience into your context, as opposed to trying to give them a bunch of context so that they can chew the cud for you and give you the…”

“If you look into the ocean of product marketers, it's kind of like shopping at Ross. It is not a job that demands a lot of really deep first principles thought from people in the job.”

“All alpha, all outperformance relative to the index comes from anti-patterns. Patterns are the things people do over and over again... None of it is predictive of success. It's the anti-pattern.”

“No matter how hard you try, if you have picked the wrong market, if you have built the wrong product, There's no amount of hard work that's going to change the fact that the market doesn't want what you have.”

“People are conditioned by the messaging around startups to believe that if you only persist, that if you only work hard enough, you will find success. And that is just obviously not true. If you look in the rearview mirror, if you look at the data, many, many,…”

“Great founders don't build markets. They find markets that exist and then they quickly raid those markets.”

“And I think like this concept of Always, always pushing or squeezing the last bit out of a product, a technology, an opportunity, or a team is a hallmark of the highest performing teams and companies.”

“If the answer is what we met in the incubator six months ago, And we decided to start a company together. I'm like, mmm, like yellow flag because you guys don't have high trust yet. You haven't spent enough time living life together. You don't have shorthands …”

“Your odds are improved When you spend time seeing high growth companies from the inside, seeing them go from zero to a hundred, zero to a thousand, whatever metric you want, but watching the chaos and the insanity and the intensity that exists only in hyper gr…”

“Don't do the income statement if there is work to do over here on the product, because you can always clean the income statement up later, but the minute you leave a crack for a competitor to come in and steal your lunch is gone. And you just have to have that…”

“Being in Silicon Valley in the middle of what is effectively Florence during the Renaissance, Where we are creating some of the craziest things that human beings have ever, ever created. To be alive at this time, to be a part of that creative explosion is such…”

“When you ask Anybody who's good, would you have me make it easier for you? Or would you have me give you more work to do so that it's uncomfortable? The highest performers, 100% of the time say, I would have you give me more work. I would have you load me up. …”

“Parker runs payroll for the, for all 5005 people don't even believe us on this. They're like, there's no way that Parker personally runs payroll for 5500 people. The answer is you're wrong. He really does.”

“Founders should be maniacal about some arbitrary thing in the product. And never, ever let go of it, because it gives them the perspective on the system that they'll lose the day they give it up.”

“You just imagine this is the first time in kind of the recent history of the concept of performance management in companies where there is an orthogonal input that can really upset with facts how people are doing this.”

“And, like, even worse is a dividend, because, like, now I can't even do that. I'm just gonna, like, literally just gonna give it. I don't know what to do with this money. I'm just gonna give it back to you. Like, what would I do with this money? There's like s…”

“There is some new stuff coming from the company that's not directly AI related, but is about really scaled data, like super high scale data. We've already built this like really beautiful data platform underneath Rippling. It's kind of like our AWS, like we're…”

“GitHub can't do this because GitHub doesn't know who you've promoted. They don't know who did well. They don't know who you've had to let go of for performance reasons. Salesforce doesn't know that either. And so, like, I'm sure there's gonna be really cool, l…”

“One thing that's really clear about successful CEOs is that they don't ever really worry about the downside of their strengths. Like they just go almost blindly, just like at the business, applying their instincts.”

“Everybody who starts a company is almost definitionally narcissistic and sort of believes that they are not subject to the statistics.”

“The third time you start the company, you're like, fuck that. Like that doesn't matter. What matters is I got to get the right product into the hands of the customer immediately. And I've got to test it in market and I've got to focus on sales and win rates. A…”

“What if I look like an asshole is a fundamentally egomaniacal question. It's a terrible question to ask. The right question to ask is what's it going to take to win?”

“I find that executives need to deliberately oversteer in the direction they want, even to the point of it being a little crazy, but it's because they are the sole tension on the line of tighter constraints, higher bars, harder, you know, harder standards versu…”

“Like, the vast majority of executive decisions are coin tosses.”

“Hiring managers should not ask someone else who they should hire. They should simply ask for objective inputs to the decision, and then they can make the decision themselves.”