“I deliberately understaff every project” | Leadership lessons from Rippling’s $16B journey

It is really important to me that we feel that we've deliberately understaffed every project at the company. If you overstaff, you get

company. If you overstaff, you get politics. You get people working on

politics. You get people working on things that are further down the priority list than necessary. That is

poison. It's wasteful. It slows you down. It creates crust. You've been a

down. It creates crust. You've been a longtime COO at Ripling. Recently, you

moved into CPO, chief product officer at Ripling. Something you talk a lot about

Ripling. Something you talk a lot about is that extraordinary results require extraordinary efforts. If you want to be

extraordinary efforts. If you want to be in the 99th percentile in terms of outcomes, it's going to be really difficult. You got to sort of remind

difficult. You got to sort of remind people that if they ever find themselves in the comfort zone at work, they are definitely making a mistake. It's

supposed to be really freaking exhausting. You're a big fan of

exhausting. You're a big fan of escalating issues.

>> Fundamentally, the most selfish thing you can do is withhold feedback from someone. When you think a thought that

someone. When you think a thought that would help someone improve and you avoid giving it to them because it would make you uncomfortable, well, you're optimizing for your own comfort. And

it's fundamentally selfish. So many

people have teams that are not functioning incredibly well. Teams will

always optimize for local comfort over company outcomes. The purest form of

company outcomes. The purest form of ambition and most intense source of energy in the business is the founder CEO. Every next concentric circle of

CEO. Every next concentric circle of management beyond the founder CEO has the potential to be an order of magnitude drop off in intensity. That is

[ __ ] 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 talk in Silicon Valley about never quit, but that is complete absolute venture capital [ __ ] Today, my guest is Matt McInness, chief

product officer and formerly longtime chief operating officer at Ripling. If

you don't know much about Ripling, it's a massively successful business, last valued at over $16 billion. They have

over 5,000 employees, and Matt has been instrumental to that success. He's also

got a really rare combination of brutal honesty, a ton of experience building a very complex and very successful business, and being able to clearly articulate what he has learned really

well. Matt shared a lot of insights and

well. Matt shared a lot of insights and advice that I've not heard anyone else on this podcast share, and I left this conversation feeling that every leader 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,

conversation. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It helps tremendously. And if

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Matt, thank you so much for being here and welcome to the podcast. Thank you

for having me. I want to start with something that I know is really important to you, something you talk a lot about that I don't think people hear enough on podcasts like this, which is that extraordinary results

require extraordinary efforts.

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 Carvana, which as a company also doesn't get enough credit for how much of a tech

company it actually is. super

interesting and I think as a general framework for me not just and a lot of what I say with you today is not really specific to product in any way um we should actually talk about that it's

like the product function is an instantiation of like the general concept of management like being a chief product officer is not that different from being a chief whatever officer you have to apply the same frameworks and

concepts to get people to achieve goals together but one thing that is like absolutely universal that I think we honestly I think we forget get it in Silicon Valley where a lot of people don't sort of internalize it is that if

you want to accomplish something truly extraordinary, if you want to be in the 99th percentile in terms of outcomes, it's going to be really difficult. Like

it's going to be really uncomfortable.

And you got to sort of remind people of that that if they ever find themselves in the comfort zone at work, they are definitely making a mistake. Like they

have definitely screwed up somehow. It's

not that uh it's not that an extraordinary effort is sufficient to an extraordinary outcome, but it is 100% true that uh it is necessary. And so I

do use that framework as a sort of guiding principle in my own leadership.

>> To make this even more real for people, what are examples of moments that were extraordinarily hard?

>> It is not about any sort of grand single story. I think the truth the story is

story. I think the truth the story is actually told through a thousand little things. And so for me, the story is told

things. And so for me, the story is told through a thousand Jira tickets, not through a thousand grand events. The

extraordinary effort thing is is is an reminder that like it's supposed to be really freaking exhausting. It's

supposed to be. So, like on Friday night when you get hit with an escalation, on Friday night when you get sort of, you know, hit with a bunch of um new bugs from someone in the engineering team

that you've got a triage, those are the moments where great players and great teams are separated from good players and good teams. And it's so easy to say

this at a company like Ripling because because we're winning like as a company for all of our foibless and we should spend time today talking about where things are not perfect and not great but the growth rate of the company on the on

the revenue foundation that we have is extraordinary like really really compelling and it it gives you as a leader the air cover to get up in front of your team and say hey guys I need the

last ounce of oil that you've got left and if your company's not growing very quickly if things aren't that great, if your growth rate is 30% or 40%, you know,

it doesn't feel as good as a contributor in that business to like lean in and give everything you've got on Friday or Saturday or Sunday because you don't know that it's going to yield much. And

so extraordinary results, outcomes demand extraordinary efforts, but if there's no chance at an extraordinary outcome, it's very hard to

get the extraordinary effort. And so I like to remind people at Ripley at least like it's so rare to have the opportunity to be able to be a part of a team where the extraordinary effort that

you do put in on Friday or whatever whenever it is is actually contributing to an extraordinary result. It's a it's a it's a very special and rare thing and it gives me a superpower as a leader because I can lean on that when I you

know when I'm ringing the oil out of somebody who's in the bored and tired zone. I saw the same thing actually at

zone. I saw the same thing actually at Airbnb with Brian Jesy. It always felt like things were going great and like maybe we could take a break after something we shipped was killing it. And

it always felt like the opposite. It

always felt like how do we press the gas pedal further? How do we go faster? How

pedal further? How do we go faster? How

do we go bigger? There's never like a moment to take a break. I spent seven years at Apple and learned under Steve Jobs, you know, when he was the CEO,

learned what we called the death march, which is what we did to the engineers.

It was like as soon as you shipped one version of the the iPhone, like you were just immediately thrown into the into the pit of building the next one and there was no break. It was just it was

just relentless. And talk about an

just relentless. And talk about an extraordinary outcome at the end of the day. Uh there is no relief. It just like

day. Uh there is no relief. It just like every in a competitive market and and if the market is valuable, it's competitive. No question. If you leave

competitive. No question. If you leave anything on the field, if you sort of leave a crack for your competitor, like 100% chance they're going to go fill that crack. And so you have to be

that crack. And so you have to be relentless. There can be no relaxation

relentless. There can be no relaxation of the organization. It doesn't mean people can't come and go or people can't take vacations or sort of live their lives, of course. And you can't it's not like people are human beings. You can't

grind the individuals down, but the team as as a collective group of people has to be sort of on the ball all the time.

There can't be a break. And if you leave one, uh, you're just begging for the slightly more hungry competitor to come in and eat your lunch. And you know,

that's the beauty of capitalism.

Also, very counterintuitively and um, maybe like the more optimistic perspective here is when you do give your team space to just twiddle their thumbs, bad things start to happen.

Morale actually dips. In my experience, people get distracted. They're like, "H, what are we even doing? It's not

interesting. I find that keeping people busy and motivated and fired up, even though you may think they'll be happier taking a like many week break and slowing things down, I find they get

more morale actually goes down in those exper moments.

>> Here's the so here's a management framework that I use fairly often. Um,

as an executive, you don't know how to get any decision exactly right. It's not

knowable. You don't know how much budget to allocate. You don't know how many

to allocate. You don't know how many people to put on a project. you don't

know how to set a deadline for when you're going to ship something. But of

course, you have to set some default. So

you you make your best guess and then you manage to that best guess and you learn as you go because in software development and in in business in general everything's emergent. It's that

these are not things that are knowable top down or a priori and so you take a best guess and knowing that you're not going to get the right answer. you need

to decide whether over steering or under steering relative to your perceived midpoint is um is better. And so let's talk about staffing. Like when you staff

a project, is it better to overstaff or is it better to understaff knowing that you can't get it right? Well, it's

better to understaff. If you overstaff, you get everything you just said. You

get politics. You get people working, I think most importantly, on things that are further down the priority list than necessary. you have

like 20 things on a stack rank list and like you know that you got to do the top five, but the next 15 down it's kind of ambiguous, but you've overstaffed the project. So like the next 10 things down

project. So like the next 10 things down are getting worked on before you even know if they're necessary. That is

poison. It's wasteful. It slows you down. It creates crust. And so it's very

down. It creates crust. And so it's very clear that understaffing is less evil than overstaffing. In this particular

than overstaffing. In this particular framework, the advice is understaff deliberately always. And then the wisdom

deliberately always. And then the wisdom the wisdom element is to know not to under understaff and sort of knowing the difference between those two things. And so that's

the way we work at rippling. Everyone is

constantly asking for more resources.

And of course where we can afford to and where it's appropriate, new resources arrive, but it is really important to me that we feel that we've deliberately understaffed every project at the company. There's a previous guest, I

company. There's a previous guest, I forget who this who this was. They use

this metaphor of they want their team to be dehydrated to always be wanting more water and then eventually they're too dehydrated and okay let's we need someone to help. Interesting. Yeah,

there's a line along the lines of extraordinary efforts. I want to make

extraordinary efforts. I want to make sure I read because I think this is really good. This may be a way to

really good. This may be a way to summarize what you're saying that good teams get tired and that's when great teams kick the good team's asses. Yes,

this was a quote actually from Sil and he found it from a from a women's um basketball team coach and it is it is to my point earlier about like you got to

run the engine at in in the red line at all times because the minute you let your guard down, the minute you slow down, the minute you relax, the minute you leave a crack for your competition, the great teams are going to come in and kick the good team's ass. And it's like,

you know, sports, I'm not a very sporty guy, but sports analogies are sort of irresistible because at the end of the day, business is a game and none of this matters. We're not going to carry it to

matters. We're not going to carry it to the grave. It's like you're here, you're

the grave. It's like you're here, you're here to do this stuff because it somehow fulfills you while you're on the planet.

And I love the sport of business. And I

find that that sports notwithstanding the fact that I watch very little of it isn't is a very that and military you those are very ripe sources of parallel concepts to apply in leadership. I find

also those most intense stressful long nights are the moments you remember most and remember most fondly back to when you're building something. The key

though is that it has to go well as you said if you are succeeding and winning all of this is romantic in the end and nostalgic. remember that time we built

nostalgic. remember that time we built this thing and worked late nights and shipped this thing. If it doesn't go anywhere, you don't you don't feel that.

So, I think that's a really important component of this is you need to be winning and succeeding.

>> I mean, one thing that I've learned from Parker is Parker is our CEO at Rippling.

He, you know, uh he said you don't you don't really learn from your mistakes, you learn from your successes. And I

it's like you do, of course, and he would admit you you learn a bit from mistakes. But I do think that this is

mistakes. But I do think that this is sort of uh feel-good [ __ ] that you know it's like well you know you didn't succeed but you know at least you learned something. I've had failures

learned something. I've had failures like when I look back at the nine years I spent working on Inkling from day one in 2009 until we sold that business to a

private equity firm in 2018 up the curve of Silicon Valley coolness back down the other side into obscurity. Like of

course I learned and grew a ton during that time, but in now what I think is six or seven years, I'm trying to do the math, seven years coming up on at Ripling, I've learned so much more

because I've seen success. Like I've

seen rapid, wild, crazy, offthecharts success of the business. And uh it's more informative. Like there's more to

more informative. Like there's more to glean from seeing how it's done right than there is to glean from seeing how it's done wrong. If I tell you you're going to get on an airplane and one maintenance technician has seen it done right a 100 times and the other maintenance technician has seen it done

wrong a 100 times but he learned from his mistakes like but still hasn't had any success himself. I mean give me a break. There's not even a comparison

break. There's not even a comparison which plane you're going to feel more comfortable on. And so I do think the

comfortable on. And so I do think the like learning from your mistakes thing is a bit of a feel-good trope that actually has very little substance in reality. It's it's and it's why as an

reality. It's it's and it's why as an early career product manager or it's it's why like frankly at any stage of 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 at a resume and I see that someone's joined um they were at like

really good companies when those companies were super exciting and in crazy growth mode. I'm like I instantly want to interview that candidate because I want to hear what they learned from being part of a winning team. And that's

um that's sort of one of my go-to heruristics when I'm looking at candidate profiles. And I think it's an

candidate profiles. And I think it's an undertold trope like sorry not an untold trope. It's a It's a piece of advice

trope. It's a It's a piece of advice that I don't think people embrace enough in the valley that like success begets success and you should chase success.

Speaking of success and learning, you've been a longtime COO at Ripling and the reason you're here uh recently you moved into CPO, chief product officer at

Ripling, uh which is very exciting and very rare. I don't see a lot of CEOs

very rare. I don't see a lot of CEOs moving into product. Let me ask you why that why did you move into into that role? I feel like you've been killing it

role? I feel like you've been killing it at CEO. Maybe that's the reason. Be

at CEO. Maybe that's the reason. Be

careful what you're good at. And also

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 um I'll tell it because I think it explains why, you know, why I'm making this transition, but this isn't really about me. I think it's sort of a pattern that

me. I think it's sort of a pattern that your listeners would find useful.

In general, your best executives are the ones that you can mostly toss into any challenge and they will bring

order to chaos. They will fix the thing.

And I do appreciate the terms that people have used at Ripling for me, you know, talking about McInness's injured

birds where at any given moment some function is in disarray or in jeopardy and I go and focus very carefully on

that function to get it back in order.

batting 800 maybe, you know, like not always wild success, but I did that any everywhere except R&D. I

would be wor I would, you know, think about helping out with components of the sales organization like our channel team or I spent time, you know, building out the recruiting function a few times when

it needed to be sort of uh rethought in response to our growth. Um, and but it never R&D. And so I I sort of I I would

never R&D. And so I I sort of I I would have my feet up on the table looking out across the floor at this dumpster fire off in the distance just sort of emitting smoke and wondering if someone

was going to go in and deal with that.

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 you're like [ __ ] that that architecture is not right or this you know they're not measuring adoption

correctly. From the outside, I actually

correctly. From the outside, I actually had quite a few criticisms that I could blob in. And um what happened at Ripling

blob in. And um what happened at Ripling was um we made some hiring mistakes. I

think the folks that we had in those roles would agree that they weren't the right people. We had a hiring mistake in

right people. We had a hiring mistake in engineering leadership where the product leader at the time had to sort of run engineering. We subsequently had a

engineering. We subsequently had a mistake in uh in product hiring and uh a lot of us had to sort of pitch in and Parker and I sort of stared at each other uh through two years of this kind

of disarray or this chaos or this agony of of things and just never really having good executive leadership over both engineering and product at the same time. And um I remember Parker sort of

time. And um I remember Parker sort of Parker sort of slumped down in his seat and said, "Ah, [ __ ] I have to run another search." And I said, "No, like

another search." And I said, "No, like the gig's up. I'm going to go do it."

and he really sprung up in his seat.

He's like, "Really? Like, you'll go do that?" I'm like, "Dude, this is what

that?" I'm like, "Dude, this is what this is what the business needs." And so that's what I did. And that really started about a year ago in sort of I realized I was going to do it and expressed that to Parker in December. I

really took it on in January of 25. And

so it's been 11 months of learning. um

jumping into the product role when the product function itself although staffed with really talented people wildly under understaffed and without a single

spiritual leader on top of it to drive consistency and process excellence had become locally optimized but globally incoherent and if you know Conway's law

you are destined to ship your org chart and so with a locally optimized as globally incoherent team. You had a locally optimized, globally incoherent product experience that needed to be

resolved. And so my efforts over the

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

leadership, uh, hiring and firing. I

mean just doing the sort of clean up on aisle 3 that needed to be done even though a lot again a lot of the people in the in the team were quite talented and doing an excellent job of managing their specific domains. Jumping into the

product role has been like quite eye opening. Um,

I feel a little bashful about the naivity of my view from the outside a year ago.

Product teams have a hierarchy of needs and we like to sort of point at the failures to meet elements of that hierarchy higher up the

triangle and sort of impugn the failure of that organization for not as an example measuring adoption metrics very

carefully and not closely tracking those metrics as a means by which to drive execution. When I jumped in, I was like,

execution. When I jumped in, I was like, man, you know, we need to establish some some basic standards for test coverage.

We need to establish some basic standards for how we do what I call a factory inspection on a product once it's ready to roll off the assembly line. Do we have a checklist for what we

line. Do we have a checklist for what we call product quality? And what does product quality mean? Those basic things weren't there. And so, the idea that we

weren't there. And so, the idea that we should be spending time measuring adoption metrics is absolute insanity.

you're skipping a lot of steps between here and there. And so we have made great strides and I think it's translating to product quality

improvements for our customers. But I

feel as I said a little dumb for the way I was thinking about it before I jumped into the deep end. There is just no excuse as an executive for sitting outside of the mess and thinking you

know the answers. It's a it's a cardinal sin as an executive to do that. you need

to go and see. You need to be in the boiler room. You need to study the

boiler room. You need to study the system bottom up and um and develop 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

incredibly well. And hearing from someone that is not a longtime product person come in and try to fix these problems, I think is really useful and interesting for people to hear. to to

dig into this a little bit more. Um was

the big lesson and kind of uh eye-opening moment that there's a lot of kind of foundational work that needs to happen to achieve this outcome that you're trying to achieve which is measure uh engagement and adoption.

Well, is it like tracking and metrics and data science? Is that kind of the in the lesson there? The lesson is that everything

must be done in its time and order and you can move really really quickly. Uh

you can you can there's no sort of excuse not to move with urgency on all of these things, but you got to do them in order. And you have to you have to

in order. And you have to you have to lead bottom up. Like you got to lead from the specific circumstances you

observe. And I think for me, one of the

observe. And I think for me, one of the best things that's happened over the last 11 months is that I've gained

a greater trust in my own instincts that that the that the sort of patterns I've matched across other functions do indeed

apply in product. But I have both the advantage and disadvantage of not having led a product function before and therefore must think about every problem from first principles. I have no choice.

I can read [ __ ] on the internet. I can

like listen to clear thinkers on topics and import their ideas, but I'm very reluctant to import an idea without breaking it down into its constituent parts and figuring out how it applies at

Rippling. And so I don't actually give a

Rippling. And so I don't actually give a [ __ ] about adoption metrics uh as a matter of principle. I care about

adoption metrics when I care about adoption metrics. Like I realize that

adoption metrics. Like I realize that that's a tautological statement, but 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, because it's in a really good place from a usability standpoint. It's very well instrumented.

standpoint. It's very well instrumented.

It's got like very happy users. Um it's

got an awesome growth profile. And so we should we should be really focused on the adoption metrics because I think that's going to be an important ingredient to low churn over time. You

know, removing friction from the implementation process as an example.

There are other parts of our product where I would say I don't care at all about adoption and am much more focused on foundational things like I said earlier test coverage or whatever just to make sure that the thing is stable

and good and delivering exactly what it's supposed to deliver to deliver once it's adopted. Now that you're on the

it's adopted. Now that you're on the inside of the product team, what's something that you think people outside of product, say Matt two years ago or other, I don't know, go to market leads,

other execs, uh, should hear need to understand about product that they don't until they're on the inside. I'll give

you another framework that I like to use. In the financial world, there's

use. In the financial world, there's this concept of alpha.

Alpha is outperformance relative to the index. So that's why you have

index. So that's why you have seekingalfalpha.com as a very popular website. What they mean by that is

website. What they mean by that is you're looking to buy something, some combination of assets that will outperform, let's say, the S&P 500 if that's your benchmark. So alpha is the

outperformance relative to the index.

And then you have the concept of beta.

Beta is just volatility. Beta is not good. A high beta stock jerks around for

good. A high beta stock jerks around for no particular reason. It's like

disorrelated with the index. It just,

you know, it's very high beta. great if

you're an options trader, but other than that, it's not really something you want in an asset. And so,

your ideal stock is a very high alpha, very low beta stock. They don't really come in that shape because alpha and beta tend to be correlated, but that's what you want when you buy a financial

asset. So, what's the analogy? I think

asset. So, what's the analogy? I think

you have high alpha people who are very valuable. I think you also have low beta

valuable. I think you also have low beta people who are also very valuable people. Um, Dennis Rodman,

people. Um, Dennis Rodman, basketball player, nut job, very high alpha. And you know, there's room on

alpha. And you know, there's room on every team for one. Dennis Rodman is a favorite of mine. It's like you can have one difficult employee who's got a ton

of upside. Um, and so this alpha beta

of upside. Um, and so this alpha beta thing, I use it pretty often when contemplating what kind of person I want

and also what kind of process I want. So

when you're building a product from 0 to one, you're probably pursu pursuing alpha. You're looking for some angle on

alpha. You're looking for some angle on this market or this customer problem where the product is actually going to provide an outsiz return relative to whatever the default solution is. When

you have a more mature product or if you have somebody in the product operations group or whatever, you probably want a more low beta environment where it's like it cranks it out. It does it very reliably. Our payroll product, we badly

reliably. Our payroll product, we badly want the payroll product to be very low beta. We really don't want the payroll

beta. We really don't want the payroll product to have any unpredictability or aberration. And so we're willing to

aberration. And so we're willing to accept more process. And here's a fundamental principle of design in an organization which is that processes

processes in a business exist for the sole purpose of lowering beta.

Processes are for decreasing volatility in the output of the system.

The the the downside of a process is that it suppresses alpha. And you have to be super super careful and judicious in the application of process in the

product team to know that you're lowering beta in the places where you want to do that without suppressing alpha in the places where you need it. And so as we've gone

through the last, you know, year of reforming the way that we build product at Ripwing, it's been a game of recognizing those places where I need to implement a touch of process, just a

touch. Other places where I need to

touch. Other places where I need to implement a very clear rigid process where I don't want alpha, I just want low beta. And so examples of this are,

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 want to bring about cultural change in a team, like look, we have we have 1300 people in our R&D organization. It's a

big ship that we have to steer. If you

want to create a moment that sticks in people's brains and sort of becomes a zeitgeist or something that they latch on to, you got to create an entity, a vessel for meaning, and then you got to

fill that vessel with your meaning. A

meme, you might say.

>> Yeah. Well, sure. a meme like a meme is actually a good example of this in common culture, you know, and um I in pop culture, I think like it's why when when people come to the table with with

with ideas from the outside, I welcome those outside ideas, but if the first thing I ask the person to do is to tell me what they mean without using those words. So when someone comes in and

words. So when someone comes in and says, "Hey, I want to do this thing on strategy." I'm like, "Cool, tell me what

strategy." I'm like, "Cool, tell me what you mean without using the word strategy."

strategy." And it forces them to break it down into its constituent parts. And if they can articulate it clearly without using that word, I know that they know what they're talking about. And if they just fumble

talking about. And if they just fumble around with the word strategy again, I'm like, okay, you actually haven't thought this through. And so with the pickle,

this through. And so with the pickle, with the product quality list, it's like I could come up with some generic term for this, but I really want a new joiner at the company to understand that this is an idiosyncratic thing to rippling.

This is unique to us. You you want to understand this thing. I also want it to become a component of common parliament in the day-to-day work of the product management and engineering teams. And so

pickle, as cheeky or silly as it sounds, was deliberately sort of angular or stood out as a vessel I could fill with a particular meaning. And so we have a product quality list. And the product

quality list is lightweight in the sense that it just articulates in the simplest ways the standards we want you to meet when you ship a product. Doesn't apply

to every product. Not every line applies to every product, but it's comprehensive and it provides me with a framework for iterating over time as we learn. And so

just yesterday, we shipped the product to Parker. This is part of our process.

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

at Rippling. If you're not aware, Parker is the sole payroll administrator for Ripling, for all 5200 employees. He

personally runs payroll always. There is

no exception for all 5200 people. He

does complain about it sometimes, but it's a remarkable achievement for the software and perhaps for him. And so he also installs any new app that we're going to install for ourselves because we dog food the hell out of everything

we build. Yesterday he goes to install

we build. Yesterday he goes to install this new application. We're about to ship a new app for feedback, allowing people to give one another feedback on their companies. And he installs it and

their companies. And he installs it and he goes in and it dumps him onto an empty screen.

And he's like, "What the [ __ ] is this?

What is this? What's going on?" Like,

"Hey, wow. Talk about fail." So I um chop another one of my fingers off. I'm

down to nine. And uh I'm like, what did we miss? What we missed was there was a

we miss? What we missed was there was a [ __ ] feature flag. [ __ ] feature flag. And I'm just I'm not allowed to

flag. And I'm just I'm not allowed to say feature flag without [ __ ] in front of it because like feature flags are the bane of my existence and the worst things in the world that constantly cause problems. Engineers put one in temporarily and forget. It's like

shims. If you're building a house and the general contractor puts little shims in places and then forgets that they put the shims there and then builds a wall over them and eventually the shim fails and all of a sudden your door doesn't

fit. Like feature flags are super

fit. Like feature flags are super dangerous and need to be managed carefully. So [ __ ] feature flags.

carefully. So [ __ ] feature flags.

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

the application. What did I do? My

reaction was uggh. Go back to the team.

Give them direct feedback. Tell them not to make that mistake again. But also ask the question, how did we miss this in the factory inspection process? And the

answer is we didn't have any line item in the pickle for feature flags. And so

I added a line to the [ __ ] pickle that said you are allowed to have one feature flag that governs your entire product at ship. It's an extreme

standard that might not be achievable but it's the standard we aspire to. This

framework, the pickle, given these lightweight checklists iterated on consistently in response to everything we learn as we go, constitutes a very

nice lightweight way to lower the beta of the system with hopefully only a modeicum of negative impact on the alpha for how we build product. And so that's, you know, you asked me a very simple

question. I gave you a very long-winded

question. I gave you a very long-winded answer, but these frameworks help me design systems that scale, you know, across one going to 2,000 technical workers.

>> 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 consonant. Okay.

consonant. Okay.

>> PQL, which how could you pronounce it other than pickle? I'm imagining all your decks have little pickle emojis and and >> the pickle emoji thing. The dancing

pickle in Slack. There's a lot of Yeah, it it lends itself to a bit of fun.

>> What I think about is pickle rake.

>> Yeah. Do you get that reference?

>> This is a roarjack test.

>> Okay. So, this high alpha low beta, I love this concept. So, the idea is depending on the team, depending on the problem, uh we need a high alpha, low beta person or actually we're okay with a lot of variance for this specific

project. Yeah, we're willing to accept a

project. Yeah, we're willing to accept a bunch of volatility in this area in exchange for the upside we get from the creativity and risk-taking of these people or these pro or the lack of process that sort of gives them the latitude to do what they want to do.

>> And so when you're hiring, you're looking for okay, is this person low beta or not? That's going to be >> for sure. I mean it's really quite a useful way you know when you you meet a candidate and

you I mean my my my modus operandi and I think you know with talk about hiring for a second I think um I've spent a lot of time with teams at

Ripling talking about how I hire 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 thousands, you know, maybe tens of thousands, I don't know. Um, it's a lot of batting practice and a lot of model training in my brain. And so I

rely a lot on my intuition, which of course HR people say you're not supposed to do. That's complete [ __ ] If you

to do. That's complete [ __ ] If you have a good intuition, you should absolutely rely on your intuition. And

um, what you have to do after you have a a reaction to a candidate when you when you're looking at um, hiring somebody is you need to decode you need to decode your intuition so that it can be expressed to other people productively.

And so one of the frameworks that I use for this is spo. Um it's a very ugly acronym. There's a hat tip to somebody

acronym. There's a hat tip to somebody out there in the universe who originally thought of this. It's not me, but I adopted it. And it's it's that people

adopted it. And it's it's that people are smart, passionate, optimistic, tenacious, adaptable, and kind. Those

five things. Six. Can't even count. I I

told you I lost a finger right when I made a mistake. So I was down one.

>> Nine. Nine to go. Spottac isn't by itself a good top- down framework, but when you're thinking about, oh, why did I not why did this candidate just like why did it not click? Why did I not like

them? Um, you go down the list, you're

them? Um, you go down the list, you're like, oh yeah, no, this person, it's that they were not excited about the idea. They weren't passionate. You know,

idea. They weren't passionate. You know,

it's like it's that they talked [ __ ] about their previous manager and that they were a victim of the performance of their last two companies. That's what it was. They're not optimistic. Um, you

was. They're not optimistic. Um, you

know, it's the the framework is super useful to evaluating people. And I think the the alpha beta framework is also super useful. When you come away from a

super useful. When you come away from a conversation, you're like, I like that guy. I think he'd be really really good.

guy. I think he'd be really really good.

Why is it that I don't think he would do a good job on this product in particular, and the answer is like, this is a high alpha product area, and he's a low beta person. Valuable, but

definitely not the right fit for this.

And so, I think it's really useful in that context as well. I love all these frameworks. You're speaking to this

frameworks. You're speaking to this audience. Frameworks, frameworks,

audience. Frameworks, frameworks, frameworks. Yeah. So, high high alpha,

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 to a different topic? When I

first started working in the product organization, I was introduced to a an interview framework or an interview

tactic that I hadn't really used much at all, I think, in my career, which is that every product person at every seniority level is given the same case

study.

And the case study is extraordinarily difficult. It requires you to think

difficult. It requires you to think about many many dimensions simultaneously to think about data propagation issues. It's gets quite

propagation issues. It's gets quite technical and um the rubric that we use to uh uh sort of evaluate performance of

that case study is um it gives you guidance on what for us like an entry- level PM looks like, what a junior mid-career senior executive PM might

look like. And everybody comes away from

look like. And everybody comes away from that interview feeling like poop, like they had failed it. Whereas on our side of it, we're like, "Wow, that person got really far." Like they saw around three

really far." Like they saw around three or four corners in a really impressive way. There was 10 they didn't see

way. There was 10 they didn't see around, but they saw around four of the hardest ones. And they were not

hardest ones. And they were not defensive when we gave them new information that called into question the validity of their solution. And they

were willing to interrupt us to ask more questions. and and and like a lot of the

questions. and and and like a lot of the sort of basic human interaction models.

I I you know, you'd never think that like giving someone an impossible task and even including the L5 person versus the VP on the same thing would be productive. And let's just say our

productive. And let's just say our recruiting team still sort of cavetes a bit about this and feels like we eliminate people too aggressively at this stage of the interview process. But

I've found the wisdom in it and think it's actually quite useful to give everyone the same simple complicated prompt and just see hand them a drill bit, give them the concrete wall and see

if they can get a millimeter or an inch into the concrete. You know, they're never going to get all the way through the wall. It doesn't matter. You're

the wall. It doesn't matter. You're

going to learn a lot. And I've found that to be kind of an eye openening new thing for me that that has been fun. I

mean, look, the joy of product and the 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 work with some of the smartest people in software. Engineers are very smart. They're not always the best sort

smart. They're not always the best sort of social, you know, uh, entities. Sales

people are awesome social entities.

They're not always the best systems thinkers. You go down the list. But the

thinkers. You go down the list. But the

magic of product management is that you kind of have to, you know, we talk about the the mini CEO. I think it's kind of a stupid misnomer, but there's some there's some wisdom there. And I think the wisdom is that you have to be a

polymath. Like you've got to be really

polymath. Like you've got to be really good at working with other people. You

got to be good at communications and articulation. You got to be good at

articulation. You got to be good at project management. You got to be good

project management. You got to be good at the science and the math and the engineering. It's really [ __ ] cool.

engineering. It's really [ __ ] cool.

And so I think one of the great joys of this job for me has been interacting with like the the tippity top of the smartest and and most polymathic people in the industry. I'll say one other

thing about what I love about leading product which is as a COO

my job was to accept the product as it was and optimize everything around that.

My job was to make sure that the product operations the in our business the interface to the insurance carriers the interface to the payment entities the government regulators that stuff all just sort of worked. It was to make sure

that our sales engine, our marketing engine, all the go-to market stuff like optimized itself around what the product was. Uh it was about recruiting and

was. Uh it was about recruiting and making sure we got people in to work on the product. You kind of go down any

the product. You kind of go down any function that isn't in R&D and I had some hand in trying to figure out how to make that function work to the best of its ability given what the product was.

And now that I lead product, I'm like, "Oh, wow. This is the high order bid."

"Oh, wow. This is the high order bid."

Not that I didn't sort of understand that, but like now I really get that product is the high order bit. If you

get the product right, it fits in the market. Uh everything else gets easier.

market. Uh everything else gets easier.

Finance is easier, sales is easier, marketing is easier, recruiting is easier, everything gets [ __ ] easier.

And so I think the other joy of of leading the product function is that uh I get to set the highest order bit in the business's success to one.

>> 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 of times I love that you're

seeing this and realizing this and uh recognizing just how uh important and interesting and uh and challenging this work is and just how awesome PMs are you know as you know a lot of people are very anti- product manager why do we

need product managers we don't need them just slow everything down all this process >> I have a distinction there which is I'm anti- shitty product managers >> that's exactly how I put If you hate product managers, you just haven't worked with a great product manager.

>> It's like, look, I I love wine. Wine's

one of my things, and I've learned a lot about wine, and one of the my favorite lines like, I don't like Chardonnay.

And I'm like, no, no, no, no, no.

Chardonnay is the most [ __ ] amazing varieties of of wine in the world. You

just haven't had good Chardonnay, you know, and uh there's a Chardonnay out there for you. Product management, like you don't like product management, you think product managers suck. It's like,

well, you just you just haven't had a good Chardonnay yet.

>> That's exactly >> once you have one. Once you have one, you know, you can't unlearn it.

>> 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 thread. You had a you've had a

this thread. You had a you've had a couple really interesting experiences of struggling to find product market fit with your own startup. You said you worked on it for nine years, you said.

>> Mhm.

>> Okay. And then with Ripling, uh, complete opposite, extreme product market fit up and to the right. What's

something you've learned about just that that you think people maybe don't understand about what it feels like, what it takes to get to product market fit, how things >> there's a line that um this venture

capitalist whose name I will not mention said which was, you know, that that um product market fit is a sort of thing where you you absolutely know it when

you see it and therefore if you don't absolutely know it, you don't have it.

And this kind of gets back to my point about learning from mistakes versus successes.

It's like, ah, man. Over and over again over the course of the many years that that I spent at Ripling, sorry, Inkling, we thought we had it. We thought we had product market fit. Maybe, maybe, you

know, and um in hindsight, with the benefit of now having experienced solid product market fit, it was so so obvious that we

didn't. And I've invested in like 60

didn't. And I've invested in like 60 companies or 70 companies. I don't know.

It's not something I actively do. Um,

but but opportunities by virtue I think of my my role at Ripling sort of show up and I talk to lots of entrepreneurs and I love it and I find it super

stimulating and I love the fresh ideas and it's just something I do as a real cherry on top of the sport that I play already. Um, but when I get the investor

already. Um, but when I get the investor updates for the guys who've been at it for like three, four, you know, years, and

I read the updates from them that I sent to my investors in 2011 and 2012, I'm kind of heartbroken.

We talk in Silicon Valley about never quit, but that is complete absolute venture capital [ __ ] The incentive

of a venture capitalist is to put money into your company and milk you dry.

They never get their money back. There

is no way for them to take that investment back.

And so the only logical desire that they would have is for you to keep trying against all odds because there is the occasional example where someone pivoted

from A to X and it was wildly different and it worked. Slack was originally some sort of a gaming company and became corporate chat. You know, Airbnb maybe.

corporate chat. You know, Airbnb maybe.

It's like there's some examples of companies having made wild pivots and succeeded, but man is that rare. I mean,

just so exceedingly rare. And I think it's important to remember like, you know, I'm 45 years old. I we're going to be on the planet. I mean, the average age of a man in the United States when he dies is something in the mid70s.

Like, I've got 20, 30, maybe, if I'm lucky, 40 years left on the planet. Very

conscious of the time that I have. And

like I don't regret what I did at Inkling. I learned a lot. It informed

Inkling. I learned a lot. It informed

what I do now. I don't think the chapter uh I'm in right now could have come without the chapters before it. And so

it's a it's a beautiful wonderful thing that I did what I did. But when I read the investor update and I'm like, you're where I was and you are not getting out of this.

The Silicon Valley try until you die mindset is not pro entrepreneur. It's pro venture

entrepreneur. It's pro venture capitalist.

And I know why that is, but I think it's important to say out loud that you should [ __ ] quit. You should reset the clock. You should reset the cap

the clock. You should reset the cap table because trust me, product market fit when it arrives is insane and it's exciting and you should pursue it and never delude yourself into believing you

have it when you don't. It is dangerous and regrettable. How's that for a

and regrettable. How's that for a speech?

Beautiful. The the uh the anti the anti-VC speech. 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 accordance with their incentives in Silicon Valley. The executives, the

Silicon Valley. The executives, the founders, the the venture cap, everybody's of course acting behaving in you know in accordance with their incentives and the venture capitalists have very strong enduring incentives

that have shaped the dynamic of how Silicon Valley works. There's nothing

wrong with that. It's just really, really important to point them out and scream at them for the 25-year-old entrepreneur who has no [ __ ] clue how

this stuff works. Trust me, the 45-year-old entrepreneur or the 50-year-old venture capitalist who have been in the game for a while, they get it. They've observed it. They know what

it. They've observed it. They know what it's like. The system is there to take

it's like. The system is there to take advantage of the people who who don't, or at least it is the easiest prey for the incentive structures, not for venture capitalists as individual people who are beautiful and wonder all of them. are just really wonderful people.

them. are just really wonderful people.

It's it's just that the incentive structures lead to some real harm, I think, in certain cases. And the thing I find is when you do quit VCs, like I'm always just like, "Hey, let me know when you're starting your next day. I'm

excited to invest." They're never they're rarely, unless they're not a great VC, rarely are they just pissed at you for like, "How could you possibly not make this work?" That's the thing like as a as a founder when it's time to

throw in the towel on your business and you're so obsessed with giving money back to the cap table I always remind the entrepreneur like hey if you're in the seed investing game your forecast is

zero your assumption on every investment is that it's going to go to zero. Any

seed investor who doesn't take that stance is is off their rocker anyway.

You know they're a very bad investor.

Um, seek investors who play the long game, who want to be in your second and third company and are willing to take a bet on the first one and let it go to zero so that you can get on with stuff.

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to get started. This begs the question 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

up. Uh here, look, history provides us with a clear guide. When you look at companies having hit it big, they hit big pretty quick. It's very, very

dangerous to be late to the party. It's

very, very dangerous to be early to the party. And the vast majority of the

party. And the vast majority of the time, that's the problem. You know, like rippling had it been started in 2014 would not be what it is today. I think

Rippling had it been started today would not be what it is five years from now today. And so I think like timing is a

today. And so I think like timing is a lot and it's very hard to control for.

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 from my lived experience, I think it's very important. One one aside, don't ask people for advice.

Ask people for relevant experience.

If you ask them for advice, they will always give it. But if you ask them for relevant experience, they rarely have any to offer. And if they don't have any to offer, then don't ask for their advice. So ask people for relevant

advice. So ask people for relevant experience. And I try to do this, you

experience. And I try to do this, you know, with with my own entrepreneurs when I work with them. It's like, let me offer you whatever relevant experience I have. And my relevant experience on this

have. And my relevant experience on this topic of when to quit is like I think we could have called it after the second or third pivot

which was somewhere around year four. It

is all is of course very important to believe in what you're building and to 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

next thing. And I think like if you're year four, year five in your entrepreneurship journey and it's not just obviously a screaming rip roaring

growth story, it's extraordinarily difficult. This is so extremely rare. So

difficult. This is so extremely rare. So

beyond even already the rare scores you're going to, you know, uh face uh from the outset that that that that that now is is going to convert to something crazy. So that's hard to hear, I guess,

crazy. So that's hard to hear, I guess, but man, it can be really liberating when you're like, "Fuck it. I'm going to do this. I have the energy. I'm going to

do this. I have the energy. I'm going to do it again. I'm just going to do it with a clean sheet.

>> That is really helpful. You have this really fun way of describing product market fit around uh receptors and drugs.

>> Oh, yeah. Yeah. I think this is like a really fundamentally misunderstood dynamic. Um

dynamic. Um when I when when founders message me and they're like, "Hey, like like my LinkedIn post and my tweet for this launch."

launch." I do it. I retweet it. I like it.

Whatever. Nobody follows me on Twitter anyways. Doesn't matter. Like I, you

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

about. Like this is not this is not how great companies are built. It can be a nucleating a nucleating event, but it's not a major thing because nobody cares about your company. Like your launch

doesn't matter. Big fat pull the pull

doesn't matter. Big fat pull the pull the slingshot back launches uh amount to the teeniest thimble of water in the ocean of noise about startups and

companies. Um, and so you just got to

companies. Um, and so you just got to build it brick by brick, bottom up. And

and these launches don't really amount to much. And so you how do you think

to much. And so you how do you think about that? Like how do you think about

about that? Like how do you think about the insignificance of your launch? Or

you think about all the effort you're putting into building a product that you believe is going to have product market fit. Well, if if you recognize that the

fit. Well, if if you recognize that the market is immutable, no amount of tweeting, LinkedIn posting, advertising is going to change whether the market

wants your product. It's not. It might

raise awareness about your product, but it's not going to change whether somebody wants it. Then you take a different mindset. You have to view your

different mindset. You have to view your startup as running an experiment in the universe to see what you get in return for that. And this analogy of like drug

for that. And this analogy of like drug discovery and binding receptors is like nobody at Janentech thinks they can market their way to better performance

inside your body. The binding receptors for that drug, they exist or they don't.

And when they build their product, their goal is to find out whether the binding receptors exist. But fate already has

receptors exist. But fate already has decided the outcome. This is absolutely true of every software product you build. Fate has already decided the

build. Fate has already decided the outcome. The market's either going to

outcome. The market's either going to latch onto your product and run with it or it's not. Do not ship the product, find a lack of success, and then try to market your way through that because the binding receptors likely don't exist.

And I I for me it was a very liberating mindset because now I just have to find the right drug and I can forget trying to convince the body to develop the binding receptors for whatever it is

that I'm building.

>> What I love about your advice here is you were an early investor in notion which is one of the classic stories of it took them I think it was four years to get to something. I think they moved to Japan, they worked on the whole thing. And so is there a lesson from

thing. And so is there a lesson from there? Like is that a rare example where

there? Like is that a rare example where it actually worked? And that's not an example to be inspired by because it's extremely extremely rare. Let's talk

about Alpha Beta again. Okay.

As an investor, you might build a checklist of things you want to make sure are true or false about a company and hope that that's going to yield the kind of like investment success you're looking for. Does it have this kind of

looking for. Does it have this kind of founder? Does it have, you know, is it a

founder? Does it have, you know, is it a CC corp in Delaware? like, you know, boom, boom, boom, boom, boom, boom. And

these checklists are all about what?

They're all about suppressing beta.

They're about avoiding avoidable mistakes. They're about bringing

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 violations. This idea that

narrative violations. This idea that like the common wisdom must be violated in some way by every company that has an outsized success.

It is absolutely true. And when I give these general observations on the patterns in Silicon Valley, the most successful businesses

inevitably violate something on that list in some really important way.

And so Notion, you can't replicate Notion's success as an entrepreneur. You can't replicate it

an entrepreneur. You can't replicate it because you're not Ivan.

You can't replicate it because you're not. You can't replicate it because it's

not. You can't replicate it because it's not 2010 when they started the company.

Do the math on that.

Or 2011, actually.

These guys stuck with it. They went

through hell. They pivoted. They went to Japan and sat in kimonos and meditated on what they were going to build. And by

hook/crook, they got to where they are today as a really wildly successful business in an extraordinarily difficult market where building businesses is virtually

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 narrative violation of persistence I don't think is a good idea for very many

people that happened to work for them and I look at it as being a function of the founding team and their specific idiosyncrasies the the absolute

insistence on craftsmanship from Ivan.

This is him that's his thing. The

takeaway lesson is not give up or don't give up. The takeaway lesson is

give up. The takeaway lesson is certainly not go do what notion did. The

takeaway lesson is that every company succeeds on the foundations of the idiosyncrasies of the founder.

The idiosyncrasies of the founder.

Ripling succeeds for almost the polar opposite reasons that notion succeeds.

But in both cases, the companies succeed on the idiosyncrasies of the founder.

And so embracing that, recognizing those idiosyncrasies, that's what great investors do. They spot that element of

investors do. They spot that element of spikiness and greatness in a candidate investment and they convert that to a commitment and then of course the

investor or the good ones accept what they get in exchange from that for the universe from the universe. I love that we went in this direction. I wasn't

planning to talk about your investing career. Uh just to give people a reason

career. Uh just to give people a reason to listen to this and maybe rewind and I want to ask another question around investing. What are some other companies

investing. What are some other companies you invested in early?

>> First of all, okay, so I I I sort of I hate the question like what are some other companies you've invested in? It's

a fair question, but the problem is like I'm going to give you a bunch of companies I've invested in that that won, you know, that are like really notable. So, what I would like to do

notable. So, what I would like to do instead of answering that question, so I'm going to give here let me let me give you some some like some bait. Like

I I was one of the first investors in notion. I was perhaps the first I don't

notion. I was perhaps the first I don't know ask Ivan um Clever, which you know had a great exit. Uh I was one of the first investors in Zenitz if you've heard of it. Um

>> heard of it.

>> I um was before I joined one of the first investors in Rippling and then more recently like invested in um here's a funny one. I was one of the first investors in deal if you've heard of

them. Um

them. Um >> I you know I I was able to exit I was 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

whatever. Um I was but more recently like you know if you've if you know um like Decagon which is doing some really cool stuff on the AI front >> killing it.

>> Um I mean Langchain like great. So those

are some companies you maybe you've heard of but like how about like I invested in macro founder was Derek Lee.

Macro's out of business. I invested in debrief Ned Roxson. It's it's out of business you know. I invested in verb data with David Herz out of business.

I'm reading from a list. I invested in um what's the number? 70 companies

according to this list where I track things and like most of them went to zero. And all those founders were

zero. And all those founders were awesome. All those founders were kickass

awesome. All those founders were kickass and all those founders put a [ __ ] ton of energy into building their businesses and they went to zero. Um and they're enduring relationships. cuz I can call

enduring relationships. cuz I can call in any of those people I think maybe with the exception of deal and you know call in a favor and and and have and I've you know I've got a few subsequent actually a lot of them joined Ripling

believe it or not so I don't know companies I've invested in is a long list and I love to give you names of companies that don't exist anymore because it's self- serving and a horrible survivorship bias to just list

the good ones. I love that answer. I

think uh I think you're being modest in the context of your hit rate is clearly very high. Uh even one or two incredibly

very high. Uh even one or two incredibly successful companies out of 70 is is a win in VC. And so uh you're doing very well. But I I think that's a really

well. But I I think that's a really important perspective. When you see

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 they've had.

>> It's good practice to ask people to give you the full list.

>> Yeah.

>> What are your favorite failures that you've invested in?

>> Oh, no. Oh, I'm not I'm not actually Okay.

>> Well, I was like, no, we don't spend time on it, but I think it's actually really a good question. Yeah. Like, what

are some of your f your best failed investments?

>> Show me the logos of the companies that didn't work out.

>> It's a really it's a juicy question.

Yeah.

>> There's a topic around this area that I wanted to spend time on and uh I haven't heard anyone uh think of things this way, which is this idea you talk about of compounding plus power law plus

entropy and how that's a really useful frame to think about business. So you

you you kick this conversation off sort of invoking the extraordinary outcomes demand extraordinary efforts line. Hat

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

explains why so few people control so much wealth. It it explains why Steph

much wealth. It it explains why Steph Curry is just so vastly better than the next guy down on the list on the basketball team. It explains why

basketball team. It explains why populations are concentrated into a really relatively small number of mega cities in the world. It's like um power law distribution just plays out

everywhere and like once you see it, you can't unsee it. It's it sort of plays out in many dynamics. People tend to think that like the world plays on a more linear relationship where the x and

y axis are sort of you know y equals x but that is absolutely not the case and the implications are profound. It's like

if you build something to 80 or 90% the y- axis is barely budged yet. You

haven't like hit the inflection point in terms of reward. And so the implication of the power law more broadly is that people who are in the top 10% the top 5%

don't just get 10 or you know 20% more reward they get 10x the reward or 100x the reward. It's really dramatic.

the reward. It's really dramatic.

Entropy the second law of thermodynamics is a very simple concept. It's the

reason your sock drawer becomes messy.

Um it's the reason that potholes form.

It's the reason we have to put so much energy into maintaining the aircraft we fly to keep them safe because they really really really want to fall apart.

And that's the nature of things. If you

if you abandon a city for a few months, it starts to go, you know, and so entropy is just this concept that [ __ ] tends toward disorder. And the the

universe, I mean, life itself is a temporary victory against entropy. You

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 if we're lucky.

What does this have to do with with product? Uh

product? Uh this is really about effort.

The only antidote to entropy, the only antidote to decay in a system is energy.

You got to inject energy. So if you have a codebase, every line of code that you add to that codebase increases the entropy of that system and demands ever more energy from human beings to go in

and tend to it to make sure it doesn't break. And if you want to achieve

break. And if you want to achieve greatness, if you want an extraordinary outcome, and in particular, if you want to be in the top 10%, top 5% on the

x-axis so that the y-axis is through the roof, then you have to relentlessly inject energy at every single step of the game.

Teams will sadly but because we are all human. Teams will always optimize for

human. Teams will always optimize for local comfort over company outcomes.

Not because they get together and think we should do that although unions do do that unequivocally deliberately.

But even in a collection of product managers or engineers what's going to happen over time is entropy is going to creep in and people are going to optimize for local comfort. Your job as

an executive, as a leader, is to fight that entropy tooth and nail every single day. It means that every time you see a

day. It means that every time you see a bug, every time you see a bug, not most 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 someone and says that they have skipped the back channel, every time you're like, you can't hire this

person unless you do the back channel.

It means that when you get into the board and tired zone on any process that you as the executive have got to demand the 99th percentile of energy because

otherwise entropy creeps in and the system decays. You have to do this. One

system decays. You have to do this. One

of the messages that I delivered recently at our big executive big, like our top 75 manager off-site that we do roughly every 18 months, um, was a

reminder that like if the if the purest form of ambition and the purest and most intense source of energy in the business is the

founder CEO.

that every next concentric circle of management beyond the founder CEO has the potential to be an order of magnitude drop off in intensity

and that is [ __ ] dangerous because if you go to two layers and it's two orders of magnitude drop off in signal and intensity that is a very dysfunctional organization so what I said to the team

was it's not that you need to buffer people from the intensity of the CEO it's that you need to absolutely mirror that intensity.

There are plenty of constituents in the business around you who will advocate for relaxing.

There is an infinite supply of people under you who will buffer other team members from the intensity of the demands.

Your job is not to be one of those buffers. Your job is to preserve that

buffers. Your job is to preserve that intensity at its highest possible level and let the buffering happen somewhere else. And that's the point is that

else. And that's the point is that entropy creeps into the system insidiously and slowly over time off your radar and you have to maintain that

intensity every minute of every day to try and fight it if you want to stay at the extreme right end of the power law 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 you. This bug sucks. I got this a broken

you. This bug sucks. I got this a broken screen. You cut like you you cut off

screen. You cut like you you cut off your finger. Maybe that's the example.

your finger. Maybe that's the example.

>> Okay. Still got them.

>> I got all 10.

>> I'll give you concrete examples. Um,

actually the joke that I sort of played on this one when I presented to the to the team was that the next sort of slide in my presentation was with the sound

effect the Slack huddle thing and Parker's icon in Slack is just he uses the generic yellow the egg.

>> Yeah. Wow. Which, you know, it's like it's funny. And so everybody knows the

it's funny. And so everybody knows the yellow egg is like is Parker. And so the next slide in the presentation was boop boop boop boop boop boop boop which is the sound that Slack makes when someone

calls you. And it was Parker Conrad is

calls you. And it was Parker Conrad is inviting you to a huddle. And then the next slide was Parker Conrad is modeling personal intensity. And the idea is like

personal intensity. And the idea is like if you know you know like if you've ever been dragged into an like I want to talk about this [ __ ] problem right now and whatever you're doing unless it's an interview like I want you to come and have a conversation with me. That

intensity is one place where it plays out. Every product team at Ripling and

out. Every product team at Ripling and we have a lot of them now have public feedback channels. I am in there upside

feedback channels. I am in there upside down on everything I find when I use those products and I just model for everybody. But this is how it's this is

everybody. But this is how it's this is how at least I want to do it, which is I don't like this. I don't understand this. Tell me why this is this way. You

this. Tell me why this is this way. You

know, boom, boom, boom, boom, boom. And

people jump in and respond. the factory

inspection process that I mentioned, which is where at the end of the assembly line, I jump out with the pickle and we talk about all of the elements. You have to record a loom of

elements. You have to record a loom of every major flow through the product. I

personally review every one of those flows. I got a backlog I got to catch up

flows. I got a backlog I got to catch up on today and and provide feedback to people always in a public channel so that every other product manager and engineering manager can jump in and see, you know, how the process has worked for

other teams. It's about modeling the intensity publicly so that other people can say, "Okay, this is how we do things around here." And it gives the reaction

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

exceptions was not like that's exhausting.

The reaction is h that is so invigorating.

So in it's like so wonderful to hear that we're going to achieve these great outcomes or at least we have a shot at doing so and that you're empowering me to follow my instinct which is to really

like push for the best result. Um the

reaction universally is is like uh what a relief that I get to go be intense because nobody in a position of leadership wants to be chill, you know?

And like what's worse than a chill boss?

No, don't work for a chill boss. Don't

be a chill boss. It's the most porative label I could give you. Chill boss or chill PM. Don't be chill. Chill doesn't

chill PM. Don't be chill. Chill doesn't

accomplish [ __ ] Be intense. Be good. Be

respectful. Be intense. Don't be chill.

And again, this advice comes from where we started, which is this is what 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?

market. Is that is that the gist?

>> Or sure. I mean, again, if you're chill and you move the X axis down 10 or 20 points, the Y-axis collapses.

It doesn't just drop 10 or 20%. The

Y-axis collapses. And this is just kind of true in everything we we do. Um, so

yeah, if you want to win, you should probably should probably try. This is what I always say to people trying to build lifestyle businesses. There's always

lifestyle businesses. There's always this idea, I'm going to build a side business. I'm going to make recurring

business. I'm going to make recurring income. It's going to be amazing. And I

income. It's going to be amazing. And I

in my experience, anytime there's a market or something shows up that's juicy and there's ways to make money, somebody's going to come at you and work harder, raise more money, and there's only so long you can maintain that.

Well, man, there's a whole other podcast episode on the concept of leverage.

>> If you sell your time, you've only got 24 hours a day to give. But if you can create a product that that scales, you know, the the the marginal cost of a

unit of that product is zero like software, it's going to be competitive, man. Sell

your time. It's not going to be super competitive, but like sell that you achieve that level of leverage and it's just going to there's it's a pretty efficient market to close out this uh threat of intensity and adding energy to

everything. Something I've heard about

everything. Something I've heard about 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 me about those two.

anything. Tell me about those two.

Fundamentally, the most selfish thing you can do is withhold feedback from someone. Who are you optimizing for when

someone. Who are you optimizing for when you do that? What are you optimizing for when you think a thought that would help someone improve and you avoid giving it to them because it would make you uncomfortable?

Well, you're optimizing for your own comfort. And it's fundamentally selfish.

comfort. And it's fundamentally selfish.

It's the most selfish thing you could possibly do is withhold feedback that would otherwise be useful to someone because you don't want to be uncomfortable. Well, that's not how high

uncomfortable. Well, that's not how high performance teams operate. So, I demand feedback and I give it. And doesn't mean that

when I give feedback, it's not open to being questioned or discussed. I mean,

of course, it is, but like when I observe something, I try to say it.

That's the feedback topic.

The the part of this that that has been interesting to me is that people withhold escalate the customers withhold. Customers don't want to

withhold. Customers don't want to escalate to me as an executive even like the the founders in whose businesses I've invested who use Rippling are reluctant to hit me up when

something goes wrong because they don't 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 system that builds the system can get better. There's no greater gift to me as a product executive than

receiving an escalation from a customer.

We have an escalations team at Ripling, which sounds weird, but it's people who are just particularly skilled at pistol whipping other people in the company to get to real root causes. Real root

causes. not like throw away the word root cause like oh we fixed the data error and shut the ticket down like no you went and you found the software that created the data error and then you found the system that created the

software that created the data error and you solved all of that back to the to the to the top escalation seems like extremely good at that at rippling so we have sort of a dedicated little team

that does this for us escalations are a gift and I and it's like if you're a listener right now on this podcast and you are a rippling customer and you have [ __ ] that you think we should know the fact that I might already know it is not

a reason for you to withhold the gift of your feedback. So, it's an attitude that

your feedback. So, it's an attitude that I take to this every day. I've got a little cue of some stuff that I've, you know, minor things that are um from the last couple of days from people who who had some nits and issues that I'm just

like I've got them queued up on my to-do list today and I'm going to take them to the product teams directly like I'd like to understand what happened here. Not in

a negative way. I just think we'll all get better if we study this one. And so,

yeah, uh escalations are a gift.

Feedback like that is a gift and nobody is ever inconveniencing me when they do it. For people that are listening to

it. For people that are listening to 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

Ripling is. I think a lot of people may not even heard have heard of Rippling. A

lot of people are like, "Yeah, it's doing great." What are some things you

doing great." What are some things you can share that are public or not public that give people a sense of just how massive this business has become? People

look at Ripley from the outside. I think

they think of us as like payroll and HR or whatever which is cool like it's it's a bit like saying Microsoft is a desktop operating system company or you know it's like every every company starts from somewhere and grows out from there.

Um we see ourselves as building the most successful business software platform in history. In fact that's the mission

history. In fact that's the mission statement of our product organization under the umbrella of the mission statement of the company which is to free smart people to work on hard problems. And like when you translate that from where we are today data, where we think we're taking things, it's like

we really do believe that like the the core of every workflow and everything that a company has to do, be it AI or manual traditional guey based software is like is who's doing stuff, who owns

it, who's accountable. And so the people record is a really important component of that. You can argue that the customer

of that. You can argue that the customer record is also very important. And of

course, some big businesses have been built on that primitive as well, but we think the people primitive is actually much more important. And the only thing that hasn't been done here is like somebody hasn't been ambitious enough to build a good business on top of that primitive. Workday is terrible software.

primitive. Workday is terrible software.

Everybody agrees on that. I think

Workday agrees on that. Good luck to them. But like they have failed actually

them. But like they have failed actually despite their success to build a really broad general purpose software platform for business software on the foundation of the people primitive. So we're going

to do that. And um we're successful because we deliver on that promise at the scale we're at today. like the fact that you can do and this is not this is not a sales pitch or sort of like an advertisement for rippling. I just think

it's important to sort of contemplate that when you bring together a bunch of disparate business processes into one system on a common business data graph an object graph a data lake with a

consistent interface you can do some pretty magical things. So we do payroll, we do HCM, we do it, we do spend, we are about to launch a new product in the category of business intelligence and

data management and there's a whole bunch of other stuff coming beyond that.

And then then you layer in AI on top of this where we alone where we alone have 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 would say gets anywhere near what we're going to show next year and it is going

to set the standard. It is going to be the most like the back flips that the AI is doing reading and writing data for the user just on our internal use cases

at Ripling is jaw-dropping. So I'm super excited about the tailwind this is going to create for us. you ask about like sort of what can I share about the success of the company what I can say there are tens of thousands of companies

that now run on rippling we're less than 1% of the market and so the you know and like the market cap at 16 billion I think now undervalues where we are from a revenue perspective by a long shot um

there there is just so much upside to to do what we're doing SAS might be deadish in terms of point solutions but long

live SAS in terms of what we're building let me follow that thread and and AI I there's been a lot of talk about AI is going to replace SAS as you maybe just said.

>> Yeah. People are going to vibe code their way to their payroll system which I you know good luck to the employees of those companies.

>> And so what I'm hearing here is the the that you actually do believe a lot of 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 continue to pay for your software. Is

that is that the gist? No, I think the gist is is a really good quote. I forget

who it's attributable to, but it's uh you know, there's two ways to make money in software. Bundling and unbundling.

in software. Bundling and unbundling.

And um you just got to get the timing right. So, this is a this is a period of

right. So, this is a this is a period of bundling.

Point. So, here's the problem. Point

solutions don't have enough data in the age of AI to be useful. You got to be able to provide the AI with a lot of context about a lot of data so it can do things. It can do joins. it can do

things. It can do joins. it can do correlations.

And so if you're a point solution, you're in you're in hard you're in hard water because you've got to now rely on data from other sources. You've got to integrate to third party systems. And when you integrate to a third party

system, even the best ones are still sort of drinking their data through a straw, which is a real problem. I mean I you know there are the the biggest HCM software

company you can think of integrates to the other biggest payroll software company you can think of through flat files via ST SFTP >> like what are they going to do? What are

they going to do? It's just never going to work. It's just no way. And so I like

to work. It's just no way. And so I like literally have no idea what they're going to do. They're just not going to build AI software. I guess like point SAS is is sort of in a in a rough sol in a rough spot especially when you cleave

two really important systems apart and say they have to integrate it's very very hard. The other thing that I would

very hard. The other thing that I would say about the world of even just like not SAS but AI software is that point solutions in the AI world are also in a rough spot for the same reason. It's

like if you're selling the shovels like OpenAI and and Google with Gemini, you can make money. And if you own the mine

like Rippling with the data, you can make money. If you're somewhere in the

make money. If you're somewhere in the middle building SA, sorry, building AI software that then tries to use the shovels from the shovel provider, but

then also needs to rent out the mine or get the ore out of somebody else's mine and start refining it. like you are in you're in a very difficult place from an economic standpoint because you're not

going to be permitted by either of those parties to build a big business on their backs. That's just not how it's going to

backs. That's just not how it's going to work. They're going to demand value

work. They're going to demand value capture that crushes your unit economics. So I look at the the like

economics. So I look at the the like landscape of AI companies that I've seen and I think you have to have a really

durable interesting insight that gives you a shot at viable unit economics to be an interesting business and that is going to kill off

80 or 90% of the stuff that I I see right now as standalone AI businesses.

So what I'm hearing here I love that you correct me when I get these things wrong and that's exactly what I want. Uh, what

I'm hearing is it's less about how difficult it is to build the SAS product. It's about do you have

product. It's about do you have first-party data that allows you to build an incredible AI product on top of what you've got.

>> Yep. Because look, SAS software is a bit flipping SAS all SAS software 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 coin sorter. You dump like you know

coin sorter. You dump like you know $20,000 for an employee in the top of the coin sorder and it figures out what goes to the government, what goes to health insurance, what goes to your 401k, what goes to you and it has to move all that money very very reliably

and seamlessly. Very challenging

and seamlessly. Very challenging software to build and manage what's it doing even that is just flipping bits in a database. And so AI

is a new way to flip bits. AI is just a new way to flip. Hopefully a way that like abstracts us a little bit further from having to think because our future

is Wall-E. It's gonna be great. Uh,

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 human. It's like a self-driving car

human. It's like a self-driving car robot. Basically, self-driving car

robot. Basically, self-driving car people build this robot that cleans your your house. It's maybe I didn't mention

your house. It's maybe I didn't mention that. It's like a a house cleaning robot

that. It's like a a house cleaning robot that just like goes around. It's like a Roomba.

>> You should get one. They're they're

expensive but incredibly cool. And

actually in Wall-E, if there's a scene where they actually have what basically what these things look like. So it's not so it's not so far.

>> 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.

news. You've seen that movie.

>> Oh man. So on this AI stuff, which is which I'm hearing is you're probably we're going to see a lot more consolidation where these point solution companies realize they need this data.

This is existential and they're going to combine and merge and bundle as you described.

>> It's possible. I am not investigator on this stuff. I think like there's some

this stuff. I think like there's some really interesting investors out there who who I think are thinking quite deeply about this and in particular uh like I the conviction which is like Mike Fernal and Sarah Gua

>> like I think those are two investors who are hyperfocused on AI and when they 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

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 they have a very deep deep deep uh set of hypotheses that they've formed over the

course of of kind of seeing every AI deal in the valley and um you know there are better people to ask this question of than I am and I uh and I think if you're an entrepreneur I recommend them to you because I think they're really

smart. Awesome. I love I love those

smart. Awesome. I love I love those guys. Also Sarah and have a podcast

guys. Also Sarah and have a podcast called No Priors that I'd also recommend. We'll point and see in the

recommend. We'll point and see in the show notes. So on this AI note, I guess

show notes. So on this AI note, I guess is there anything else that you think would be really helpful for founders that are working in this space building an AI startup to hear they think you're seeing of like here's how you need to

here's what you need to do to win in an AI company.

>> So like I actually think that if I were to give you an answer to this question right now it would be [ __ ] >> Yeah. I don't have back to my point

>> Yeah. I don't have back to my point earlier. I don't have like I don't have

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

them luck. I love that the circling back to your advice, don't ask for advice, ask for a relevant experience. And I

love that that's what your mind immediately went. I'm going to take us

immediately went. I'm going to take us to AI quarter, which is a recurring segment on this podcast. And the

question is just what's one way you've found AI to be useful in your work dayto day? Is there something that you found

day? Is there something that you found it unlocked in having >> I mean it's not a super exciting thing but I'll say like where I use so I like one of the most important functions that I perform as an executive is the

synthesis of ideas and the ability to communicate those ideas very clearly to people. So when I talk about like the

people. So when I talk about like the product quality list and the pickle as something that we've come up with internally I do turn to um to AI chat GPT and Gemini where I I take like a

really um let's say angular view of some topic and I give really I write the essay for the AI and I'm like look this is the

crisp idea I want to communicate help me come up with piffy ways to articulate these things and 80% of what it outputs is trash. It's just like sort of

is trash. It's just like sort of middle-of the road average lowalpha junk, but it is a thought partner, a non-judgmental thought partner where

like in 20% of the stuff it comes out with, I'm like, it's pretty good. That's

a new word I didn't think of that does kind of hit the nail on the head for this concept. And so if you if I believe

this concept. And so if you if I believe that my job is is to sort of bring brains along on the journey for some sort of change that I'm trying to bring about, then the most important tool is

language. And I do find that that chat

language. And I do find that that chat GPT and Gemini do a great job of helping me refine how to articulate the concepts that I want to to articulate. They are

not useful in coming up with the ideas themselves. That's an awesome tip. I

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 writing and words and language. I have not spent a lot of time

language. I have not spent a lot of time with Claude. I do I have used it. Um,

with Claude. I do I have used it. Um,

but by virtue of this conversation, I'll probably go give it >> There we go. They're they're all great, but uh there's something about Claude that is just at writing specifically is much better. Um but they're all getting

much better. Um but they're all getting 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 round, is there anything else that you were hoping to share? Anything

else you wanted to touch on or leave listeners with? We've we've spent a lot

listeners with? We've we've spent a lot of time talking about intensity and the grind and the need to just always be

operating at the 99th percentile.

And um I think if you listen to that in a vacuum, it's very easy to believe that that intensity is

soul crushing that that it's a negative um that it's maybe not something that you want.

And I I think there's a backs stop for me that I didn't talk about today that I think I I is important to share which is that life is amazing.

That like the fact that we all exist on this blue marble drifting through space and time that we are some weird instantiation of consciousness each of us. and that

you're here for such a short period of time whittling your stick, doing something that like if you remember how insignificant we are and all of this is,

it brings this levity to what we do and and to the work we put into building this because this is like

rip like Silicon Valley in 2025 is is Florence in the Renaissance.

It's crazy. Like the amount of creativity and insane invention and progress that's happening for our species right now in this place is

absolutely unparalleled in all human history. You got to zoom out and

history. You got to zoom out and appreciate that magic. And so then you turn around, you're like, "Fuck, I got to work on Friday night, right? Like I

I've got to go give it my all. I got to go compete in the arena of business."

Just you have to you never you have to never forget that number one none of this matters and number two it is an absolutely beautiful and amazing

phenomenon that we get to be alive doing this right now. So like play the sport play it with everything you've got but never forget that it's just a sport and

that none of it matters and it's super important as a counterpoint to the 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 person when I saw it. Yeah.

>> 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 three books that you find yourself recommending most to other people?

>> Uh, okay. Two or three books. You You

give me a heads up on this. So like one one book is conscious business. I don't

have conscious business in front of me because it's actually at the office because we have conscious business reading club at rippling and every member of my current my product leadership team is going through this right now. Conscious business Fred

right now. Conscious business Fred Kaufman it's been used in many businesses LinkedIn most notably as a framework for thinking about effectively it's a user manual for human beings. So

if you are a leader, a manager, an executive whatever particularly younger, like people in their 20s and 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 my board at my previous company. I took way too long to

previous company. I took way too long to take him up on the advice. Wished I had read it sooner. Highly recommend

conscious business. Changes your life.

Number two, thinking and systems. Donna Meadows, I always mispronounce her name. Donella

Meadows. She died partway through writing this manuscript. Her fellow

professors picked it up and finished it for her. It is the best generic

for her. It is the best generic framework for thinking about like how systems work. You will extrapolate from

systems work. You will extrapolate from this book to every aspect of your life after you read it. Um, and then the third is classic 1960s the effective executive. It's an anacronism. It uses

executive. It's an anacronism. It uses

weird pronouns for the secretary and the executive. I'll let you guess which

executive. I'll let you guess which ones, but like the book itself is so chalk full of simple, enduring advice on how to be effective

at leading teams. And uh the good [ __ ] is the stuff that's been in print for 70 years and that's that's one of them.

>> Beautiful. I love the first one is you don't have it because you you're using it with your team constantly. You you

mentioned at one point uh before we started recording, you have like eight copies of that book that you just give out to everyone.

>> Yeah. And we hand it out like candy.

>> Okay. Is there a favorite recent movie or TV show you've really enjoyed?

>> Um, yeah. So, I'm a little embarrassed by this answer, but I'm going to be honest, please. Um, there's a a new

honest, please. Um, there's a a new series called Heated Rivalry, and it's about I'm Canadian and I'm gay. So, it's about two hockey

players um in Canada, rivals between the Bruins and the Maple Leafs, although they don't use those names, who are like just heated rivals on the ice, and it's a huge thing that the the world is

watching, but actually they're secret secretly in love with each other, and they start hooking up. And it's been labeled by the media as smutty, but delightful. And uh I would say that's

delightful. And uh I would say that's accurate. So it might not be for

accurate. So it might not be for everybody, but it is a it is a smash hit right now. It's on HBO Max and Crave,

right now. It's on HBO Max and Crave, and it's only six episodes, but uh like I said, a little embarrassing because it's very uh it's it's a little chintzy, but it's a lot of fun. It's

also really fun to see like gay people represented in the media as though they're normal.

>> And soon to be on Netflix with the acquisition if that goes through. Oh,

it's crazy.

>> Amazing. Okay. Is there a favorite product you recently discovered that you really love?

My fellow coffee maker.

>> I love My fellow coffee maker. It's got

an interface that lets you like set light, medium, dark roast. It changes

the temperature. It blooms the coffee.

It tells you how many grams of coffee to put into the basket. Um slick interface, high quality coffee. It's like it's definitely awesome. And so I have

definitely awesome. And so I have actually have one in the office and one at home and one in the garage.

>> Wow. That is a favorite product. You

have three of them in in the same space.

>> Oh, no. in the office. Okay. Fellow is

also a Ripling customer and that's like a a nice side effect when we get to >> Have they ever escalated anything to you? No. If you're listening and you're

you? No. If you're listening and you're from fellow, I want to hear all your gripes. Perfect. Two more questions. Do

gripes. Perfect. Two more questions. Do

you have a favorite life motto that you find yourself coming back to often in work or in life?

>> It's a dark one and I'll share this one sort of uh partially for the humor of it, but it's it's actually sometimes useful immediately at least. It's sort

of a moment of smiling when it happens.

is like the the the model comes from my dad who said, "Matt, nothing's ever so bad in life that it couldn't get worse."

And it's like we were going through some [ __ ] yesterday at work and we were like, "Fuck, now that happened." And I looked at the CTO and I'm like, "Dude, nothing's ever so bad that it couldn't get worse." And we had a good laugh and

get worse." And we had a good laugh and continued to brace for whatever might come next. So, not not exactly

come next. So, not not exactly uplifting, but fun to use.

>> No, that is it is uplifting. It's an

like I'm an optimist and I find myself thinking that often with my wife just like it could be worse. It could be worse than this.

>> Definitely useful >> and it might get there.

>> So let's enjoy this less worse version.

Uh final question something you shared with me is that you were a DJ when you were a younger person. Uh can you just give us a little uh DJ DJ voice to give people a sense of

>> so first of all we it's not DJ Lenny.

It's radio personality >> and yeah, I used to do the greatest hits of all time with hits from the 60s, the 70s, the 80s, and a little bit of the '9s. 1015, the Hawk. Yeah, this a you

'9s. 1015, the Hawk. Yeah, this a you can turn it on. It's very inauthentic, but it sounds good on the radio. Uh it's

cool. I did it when I was in high school. I ended up doing the midday uh

school. I ended up doing the midday uh the midday segment when uh right before I went to college. And what a gift. What

a huge gift in my most formative years to have developed like uh an ability to be in front of a microphone comfortably, you know, because here we are.

>> I love for people that weren't watching this YouTube, you like lean really close to the mic to get that to get that uh radio personality voice.

>> Yeah, you got to be able to hear like the saliva in the mouth.

>> Incredible. It's like the same person talking. Like if you're not watching

talking. Like if you're not watching this, you're like, "Where did that guy come from?" Uh that was great. You

come from?" Uh that was great. You

nailed it, Matt. Uh this was incredible.

I really appreciate you being here. I

really appreciate you sharing all this advice that I have not heard other people share. Two final questions. What

people share. Two final questions. What

do you is there some you want to plug point people to? And how can listeners be useful to you? Look, my life is rippling. I point people there. And

rippling. I point people there. And

that's this is my life's work. It's

going to be uh it's going to be a banger. So stay tuned. And um and the

banger. So stay tuned. And um and the way that you can help me is that if you're a customer, you got to tell me when you have problems cuz that's how we get better.

>> What's the way they get to you? Is there

any place you want to point people to?

>> DM me on Twitter is easy9.

You can email me my last name at rippling.com. Um,

rippling.com. Um,

and uh, I'll go that far without giving out my phone number. How's that?

>> Perfect.

>> The perfect boundary.

>> Yeah, >> Matt, thank you so much for being here.

>> It's my pleasure. Thank you for having me, Lenny. And uh, congrats on all the

me, Lenny. And uh, congrats on all the success with this podcast. It's been

great.

>> Same to you. It's always a good sign at the end of a conversation. We're like,

"Oh, I got to get me some of that stock and that got to get into that rippling."

Uh so >> it's a good buy recommended buy.

I yeah, but you're, you know, hard to get to.

>> All right, man. Thank you so much.

>> Thanks.

>> Thank you so much for listening. If you

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See you in the next episode.