"It is really important to me that we feel that we've deliberately understaffed every project at the company. If you overstaff, you get politics. You get people working on things that are further down ..."

"escalating issues. >> Fundamentally, the most selfish thing you can do is withhold feedback from someone. When you think a thought that would help someone improve and you avoid giving it to them becau..."

"[ __ ] dangerous. As an executive, as a leader, your job is to preserve that intensity at its highest possible level. You've had a couple really interesting experiences with your own startup. >> We ta..."

"needs to hear his advice. A huge thank you to Albert Scrashim and Sil Raman for suggesting topics and questions for this conversation. If you enjoy this podcast, don't forget to subscribe and follow i..."

"required with Gemini 3 in Google AI Studio. It's called vibe coding and we're making it dead simple. Just describe your app and Gemini will wire up the right models for you so you can focus on your cr..."

"growth metrics. Where other tools stop, data dog goes even further. It helps you actually diagnose the impact of funnel drop offs and bugs and UX friction. Once you know where to focus, experiments pr..."

"heat maps and scroll maps to truly understand their behavior. And all of this is powered by feature flags that are tied to realtime data so that you can roll out safely, target precisely, and learn co..."

"Talk about why that's so important, what you think people need to hear. I mean, this is a term that phrasing I actually attribute to a friend of mine, uh, Dan Gil, who's the chief product officer at C..."

"your career when you want to learn you should join a winning team. Like it's cool to go and start a company at 22, good luck to you. That the odds are not in your favor. But the folks who when I look ..."

"just what what are some surprises about this about moving into product because a lot of people imagine what it's like and then you're actually doing it. The story at Ripling is pretty interesting and ..."

"And you know the smoke takes various forms and when you're growing as quickly as Rippling is growing it's not always something that necessarily even impacts customers but it's the sort of thing where ..."

"resolved. And so my efforts over the last 11 months have been to establish, you know, like greater clarity in terms of how we do things around here, better process, better, you know, general leadershi..."

"hypotheses for how to amend the system. And that's what I've been doing. I love hearing this because so many people have teams that are not functioning incredibly well. And hearing from someone that i..."

"it's like I'll get there. And so in certain parts of our product, I really do care about adoption metrics. I care a lot about adoption metrics in our applicant tracking system, our recruiting product,..."

"asset. So, what's the analogy? I think you have high alpha people who are very valuable. I think you also have low beta people who are also very valuable people. Um, Dennis Rodman, basketball player, ..."

"low beta. And so examples of this are, let's say, our product quality list, which we lovingly at Riplin call the pickle. >> Why pickle? Yeah. So it's actually a really important thing. I think if you ..."

"just yesterday, we shipped the product to Parker. This is part of our process. When we ship a new product, it goes to Parker, who is the big admin for Ripling at Rippling. If you're not aware, Parker ..."

"Anyway, we had one. Parker installs it. They forgot to disable the feature flag. He gets a blank screen when he installs the application. What did I do? My reaction was uggh. Go back to the team. Give..."

">> Wow. Okay. By the way, pickle, is that is that like an acronym or it's just like I like this word. We're going to call it pickle. >> Product quality list. >> Product. Okay. I see. So it's the conso..."

"and it is born of batting practice meet it be super interesting to actually be able to rewind the tape on my life and and sort of contemplate how many candidates I've met in every context many thousan..."

"audience. Frameworks, frameworks, frameworks. Yeah. So, high high alpha, low beta, sometimes high beta is okay. Spo um in hiring, is there anything else that you find really useful before we move on t..."

"joy of product management and the joy of of being part of product. I think there's a bunch of joys actually. if I could give you a sort of running list, but like one of the big joys is that you get to..."

">> This is uh really great to hear. uh a lot of times people outside product don't understand these sorts of things and uh look down on product a lot of times especially you know sales folks cos a lot..."

">> Like, let's find that PM ASAP. >> No, let's find that Chardonnay ASAP that PM with with some Chardonnay. You met you touched on this product market fit point and I want to double down on this threa..."

"Beautiful. The the uh the anti the anti-VC speech. The >> I got more where that came from. By the way, it's not it's not anti-VC. It's anti- VC propaganda. >> It's the incent everybody's acting in acc..."

"of just when is it time to quit? You know, people hearing this might be like, oh man, like what are some signs that okay, it's time to it's time to wrap it up. Uh here, look, history provides us with ..."

"But when you get the timing right and the market is real and the product works, product market fit, like I said earlier, it's it's super clear. And so if I were to pick a number out of a hat, just fro..."

"be you know like to be persistent. Um but there is definitely no shame in saying look we've pivoted once or twice it's not catching I got to go do the next thing. And I think like if you're year four,..."

"Whatever. Nobody follows me on Twitter anyways. Doesn't matter. Like I, you know, I do that and then um but I think to myself like this is not what this is about. Like this is not this is not how grea..."

"goal is to find out whether the binding receptors exist. But fate already has decided the outcome. This is absolutely true of every software product you build. Fate has already decided the outcome. Th..."

"They're about avoiding avoidable mistakes. They're about bringing stability. Jeff Lewis is an investor who has many angular views on things. And I think one of his most enduring phrases is narrative v..."

"impossible in productivity. It is dominated by Google and Microsoft. Carving out your own niche in that market is just unthinkable. And so I look at notion as having succeeded by virtue of the narrati..."

"And so embracing that, recognizing those idiosyncrasies, that's what great investors do. They spot that element of spikiness and greatness in a candidate investment and they convert that to a commitme..."

"able to exit that position and then you know hopefully that company's going to zero with their criminal behavior but whatever. Um I was but more recently like you know if you've if you know um like De..."

"well. But I I think that's a really important perspective. When you see people's logos on their websites of all the companies they've invested in, you have no idea how many they've how many at bats th..."

"tip to Dan Gil. And these are part and parcel like man understanding the nature of the universe is a pretty good way to work within it. And so like power law distributions happen everywhere. It explai..."

"and I should not exist. The sun gives energy to the planet. it organizes stuff that we can eat and like we fight entropy until we lose the battle somewhere as I said earlier at the age of 70 or 80 um ..."

"of the time, every time you go and you drop it at the feet of the product manager or the engineering manager, every time in public preferably, it means that every time someone comes to you to hire som..."

"that obviously governs the outcome of everything that we build. What does that look like to pass along that intensity? Like what does that feel like? What does that look like? So, say Parker comes to ..."

"around here." And it gives the reaction the reaction from the team that received the message that that you have to you have to inject that energy every minute of every day and that there are no except..."

"success looks like because somebody that is less chill than you is going to find that crack and come after your your market. Is that is that the gist? >> Or sure. I mean, again, if you're chill and yo..."

"you is you're big on uh escalating. You're a big fan of escalating issues and also you always tell people to never not give you negative feedback, to always share feedback, to not hide anything. Tell ..."

"want to bother me. But is literally my job literally my job to find things problems and make them better. And by virtue of making those specific things better to iterate on the processes so that the s..."

"this and feeling like, man, this is so stressful and intense and just like I I don't know if I want to work this way. Give them a sense of just how successful Ripling is. I think a lot of people may n..."

"all of your business data organized into this nice neat package with a beautiful semantic layer on top of it. the AI can work magic and we have shipped nothing nothing yet in this category that I woul..."

"SAS companies that are selling individual solutions are in big trouble. The answer is implied here is this kind of compound startup idea of you need to do a lot of things for people for them to contin..."

"applications are bit flippers. Like it's a it's an interface changing Yeah. changing values in a database. What it does, >> it's really hard pro like Rippling. One of Rippling's superpowers is we're a..."

"from having to think because our future is Wall-E. It's gonna be great. Uh, speaking of Wall-E, actually, I I have this Madic robot. You have one of these? >> Uh, it's a it's like a it's a like a huma..."

">> That movie was actually quite preient perhaps with the exception of the gravity defying day beds. >> Yeah. I don't know. But that's not good news. You've seen that movie. >> Oh man. So on this AI s..."

"made the decision to sort of take that approach at the time I thought like that's kind of narrow. Uh now I'm like no no no no that was the right move and and like they it just means that they like the..."

"earlier. I don't have like I don't have enough relevant experience in the abstract to like dole out on a podcast on that topic. But I, you know, I wish them luck. I love that the circling back to your..."

"that I want to to articulate. They are not useful in coming up with the ideas themselves. That's an awesome tip. I don't know if you've played with Claude much, but I actually find Claude is better at..."

"better all the time. It's always there's always uh something new. Matt, we've covered so much ground. We've touched on everything I was hoping to touch on. Before we get to our very exciting lightning..."

"intensity that we we talked about. That is beautiful. I think about Pale Blue Dot, Carl Sean's, the whole thing. >> Just stunning photograph that literally changed the way I think about who I am as a ..."

">> Well, going in a completely different direction with that, Matt, we reached our very exciting lightning round. We've got five questions for you. Are you ready? >> Okay, here we go. What are two or ..."

"30s who are just sort of getting the hang of being a CEO or a product leader for the first time, this book is absolute [ __ ] gold. It was recommended to me by Brian Shrier at Sequoia when he was on m..."